Hoch effiziente asymmetrische Katalyse durch doppelte Aktivierung von Nucleophil und Elektrophil
Jun-An Ma Dr.
UMR 6014 CNRS de L'IRCOF, Université de Rouen, 1 Rue Tesnière, 76821 Mont Saint Aignan Cedex, Frankreich, Fax: (+33) 2-3552-2971
Institute and State Key Laboratory of Elemento-Organic Chemistry, Universität Nankai, Tianjin 300071, China
Search for more papers by this authorDominique Cahard Dr.
UMR 6014 CNRS de L'IRCOF, Université de Rouen, 1 Rue Tesnière, 76821 Mont Saint Aignan Cedex, Frankreich, Fax: (+33) 2-3552-2971
Search for more papers by this authorJun-An Ma Dr.
UMR 6014 CNRS de L'IRCOF, Université de Rouen, 1 Rue Tesnière, 76821 Mont Saint Aignan Cedex, Frankreich, Fax: (+33) 2-3552-2971
Institute and State Key Laboratory of Elemento-Organic Chemistry, Universität Nankai, Tianjin 300071, China
Search for more papers by this authorDominique Cahard Dr.
UMR 6014 CNRS de L'IRCOF, Université de Rouen, 1 Rue Tesnière, 76821 Mont Saint Aignan Cedex, Frankreich, Fax: (+33) 2-3552-2971
Search for more papers by this authorAbstract
Die Entwicklung neuer Hochleistungs-Katalysatoren für asymmetrische Katalysereaktionen ist für die Organische Chemie von dauerhaftem Interesse. Eine aktuelle Methode bei der stereoselektiven Synthese ist die Verwendung einer Kombination von Lewis-Säure und Lewis-Base. Der Synergieeffekt durch die Aktivierung mithilfe von zwei oder mehr reaktiven Zentren führt zu hohen Reaktionsgeschwindigkeiten und zu einer hervorragenden Übertragung der stereochemischen Information. Obwohl durch die unerwünschte Reaktion der Lewis-Säure mit der Lewis-Base der Katalysator inaktiviert werden kann, wird das Konzept der doppelten Aktivierung mit großem Aufwand weiterentwickelt. Das Ziel ist die Herstellung biomimetischer Katalysesysteme auf der Grundlage enzymatischer Prozesse mit cokatalytischen Metallionen. Doppelt aktivierende Katalysatorsysteme erweitern die Zahl bereits bekannter Katalysatoren beträchtlich. Die effektivsten dieser Systeme werden in diesem Aufsatz erörtert und die Wirkungsmechanismen diskutiert.
References
- 1
- 1a Comprehensive Asymmetric Catalysis (Hrsg.: ), Springer, Berlin, 1999;
- 1b Catalytic Asymmetric Synthesis, 2. Ausg. (Hrsg.: ), Wiley-VCH, Weinheim, 2000.
10.1002/0471721506 Google Scholar
- 2S. Woodward, Tetrahedron 2002, 58, 1017–1050.
- 3
- 3aM. Sawamura, Y. Ito, Chem. Rev. 1992, 92, 857–871;
- 3bH. Steinhagen, G. Helmchen, Angew. Chem. 1996, 108, 2489–2492;
10.1002/ange.19961082005 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2339–2342;
- 3cM. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290–1310;
10.1002/ange.19971091204 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 1236–1256;
- 3dE. K. van den Beuken, B. L. Feringa, Tetrahedron 1998, 54, 12 985–13 011;
- 3eG. J. Rowlands, Tetrahedron 2001, 57, 1865–1882;
- 3fH. Gröger, Chem. Eur. J. 2001, 7, 5246–5251;
10.1002/1521-3765(20011217)7:24<5246::AID-CHEM5246>3.0.CO;2-O CAS PubMed Web of Science® Google Scholar
- 3gM. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187–2209.
- 4
- 4aA. Hirao, S. Itsuno, S. Nakahama, N. Yamazaki, J. Chem. Soc., Chem. Commun. 1981, 315–317;
- 4bS. Itsuno, A. Hirao, S. Nakahama, N. Yamazaki, J. Chem. Soc., Perkin Trans. 1 1983, 1673–1676;
- 4cS. Itsuno, K. Ito, A. Hirao, S. Nakahama, J. Chem. Soc., Chem. Commun. 1983, 469–470.
- 5
- 5aE. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551–5553;
- 5bE. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092–2118;
10.1002/(SICI)1521-3757(19980803)110:15<2092::AID-ANGE2092>3.0.CO;2-M Google ScholarAngew. Chem. Int. Ed. 1998, 37, 1986–2012, zit. Lit.10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 6M. P. Sibi, G. R. Cook, P. Liu, Tetrahedron Lett. 1999, 40, 2477–2480.
- 7
- 7aJ. M. Brunel, O. Pardigon, B. Faure, G. Buono, J. Chem. Soc., Chem. Commun. 1992, 287–288;
- 7bJ. M. Brunel, G. Buono, Synlett 1996, 177–178;
- 7cJ. M. Brunel, O. Chiodi, B. Faure, F. Fotiadu, G. Buono, J. Organomet. Chem. 1997, 529, 285–294.
- 8
- 8aB. Burns, N. P. King, H. Tye, J. R. Studley, M. Gamble, M. Wills, J. Chem. Soc., Perkin Trans. 1 1998, 1027–1038;
- 8bG. Buono, O. Chiodi, M. Wills, Synlett 1999, 377–388;
- 8cM. Wills, M. Gamble, M. Palmer, A. Smith, J. Studley, J. Kenny, J. Mol. Catal. A: Chem. 1999, 146, 139–148.
- 9R. J. Kell, P. Hodge, P. Snedden, D. Watson, Org. Biomol. Chem. 2003, 1, 3238–3243.
- 10
- 10aM. Kitamura, S. Suga, K. Kawai, R. Noyori, J. Am. Chem. Soc. 1986, 108, 6071–6072;
- 10bR. Noyori, M. Kitamura, Angew. Chem. 1991, 103, 34–54; Angew. Chem. Int. Ed. Engl. 1991, 30, 49–69;
- 10cM. Kitamura, S. Suga, M. Niwa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 4832–4842.
- 11L. Pu, H.-B. Yu, Chem. Rev. 2001, 101, 757–824, zit. Lit.
- 12
- 12aM. Yamakawa, R. Noyori, J. Am. Chem. Soc. 1995, 117, 6327–6335;
- 12bM. Yamakawa, R. Noyori, Organometallics 1999, 18, 128–133;
- 12cB. Goldfuss, K. N. Houk, J. Org. Chem. 1998, 63, 8998–9006;
- 12dB. Goldfuss, M. Steigelmann, S. I. Khan, K. N. Houk, J. Org. Chem. 2000, 65, 77–82;
- 12eJ. Vazquez, M. A. Pericas, F. Maseras, A. Lledos, J. Org. Chem. 2000, 65, 7303–7309;
- 12fM. Panda, P.-W Phuan, M. C. Kozlowski, J. Org. Chem. 2003, 68, 564–571;
- 12gM. C. Kozlowski, S. L. Dixon, M. Panda, G. Lauri, J. Am. Chem. Soc. 2003, 125, 6614–6615.
- 13
- 13aE. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 3053–3056;
- 13bE. F. DiMauro, M. C. Kozlowski, J. Am. Chem. Soc. 2002, 124, 12 668–12 669;
- 13cE. F. DiMauro, M. C. Kozlowski, Org. Lett. 2002, 4, 3781–3784.
- 14K. Funabashi, M. Jachmann, M. Kanai, M. Shibasaki, Angew. Chem. 2003, 115, 5647–5650;
10.1002/ange.200351650 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 5489–5492.
- 15B. L. Pagenkopf, E. M. Carreira, Tetrahedron Lett. 1998, 39, 9593–9596.
- 16T. Ooi, N. Kagoshima, K. Maruoka, J. Am. Chem. Soc. 1997, 119, 5754–5755.
- 17D. R. Gauthier Jr.,E. M. Carreira, Angew. Chem. 1996, 108, 2521–2523;
10.1002/ange.19961082018 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 2363–2365.
- 18
- 18aA. Yanagisawa, H. Kageyama, Y. Nakatsuka, K. Asakawa, Y. Matsumoto, H. Yamamoto, Angew. Chem. 1999, 111, 3916–3919;
10.1002/(SICI)1521-3757(19991216)111:24<3916::AID-ANGE3916>3.0.CO;2-V Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3701–3703;10.1002/(SICI)1521-3773(19991216)38:24<3701::AID-ANIE3701>3.0.CO;2-D CAS PubMed Web of Science® Google Scholar
- 18bM. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem. 2003, 68, 5593–5601.
- 19S. Yamasaki, K. Fujii, R. Wada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 6536–6537.
- 20R. O. Duthaler, A. Hafner, Angew. Chem. 1997, 109, 43–45;
10.1002/ange.19971090106 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 43–45.
- 21G. K. Friestad, H. Ding, Angew. Chem. 2001, 113, 4623–4625;
10.1002/1521-3757(20011203)113:23<4623::AID-ANGE4623>3.0.CO;2-G Google ScholarAngew. Chem. Int. Ed. 2001, 40, 4491–4493.10.1002/1521-3773(20011203)40:23<4491::AID-ANIE4491>3.0.CO;2-8 CAS PubMed Web of Science® Google Scholar
- 22T. Hamada, K. Manabe, S. Kobayashi, Angew. Chem. 2003 115, 4057–4060;
10.1002/ange.200351778 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3927–3930.
- 23S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763–2794.
- 24M. Nakajima, M. Saito, M. Shiro, S. Hashimoto, J. Am. Chem. Soc. 1998, 120, 6419–6420.
- 25T. Shimada, A. Kina, S. Ikeda, T. Hayashi, Org. Lett. 2002, 4, 2799–2801.
- 26A. V. Malkov, M. Orsini, D. Pernazza, K. W. Muir, V. Langer, P. Meghani, P. Kočovský, Org. Lett. 2002, 4, 1047–1049.
- 27A. V. Malkov, L. Dufkova, L. Farrugia, P. Kočovský, Angew. Chem. 2003, 115, 3802–3805;
10.1002/ange.200351737 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3674–3677.
- 28
- 28aS. Kobayashi, K. Nishio, Tetrahedron Lett. 1993, 34, 3453–3456;
- 28bS. Kobayashi, K. Nishio, Synthesis 1994, 457–459;
- 28cS. Kobayashi, K. Nishio, J. Org. Chem. 1994, 59, 6620–6628.
- 29
- 29aK. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron Lett. 1998, 39, 2767–2770;
- 29bK. Iseki, S. Mizuno, Y. Kuroki, Y. Kobayashi, Tetrahedron 1999, 55, 977–988.
- 30
- 30aS. E. Denmark, J. Fu, J. Am. Chem. Soc. 2000, 122, 12 021–12 022;
- 30bS. E. Denmark, J. Fu, J. Am. Chem. Soc. 2001, 123, 9488–9489;
- 30cS. E. Denmark, J. Fu, J. Am. Chem. Soc. 2003, 125, 2208–2216;
- 30dS. E. Denmark, J. Fu, Chem. Commun. 2003, 167–170.
- 31
- 31aK. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, Y. Kobayashi, Tetrahedron 1997, 53, 3513–3526;
- 31bK. Iseki, Y. Kuroki, M. Takahashi, Y. Kobayashi, Tetrahedron Lett. 1996, 37, 5149–5150.
- 32R. M. Angell, A. G. M. Barrett, D. C. Braddock, S. Swallow, B. D. Vickery, Chem. Commun. 1997, 919–920.
- 33I. Chataigner, U. Piarulli, C. Gennari, Tetrahedron Lett. 1999, 40, 3633–3634.
- 34
- 34aM. North, Tetrahedron: Asymmetry 2003, 14, 147–176, zit. Lit;
- 34bJ.-M. Brunel, I. P. Holmes, Angew. Chem. 2004, 116, 2810–2837;
10.1002/ange.200300604 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 2752–2778.
- 35E. J. Corey, Z. Wang, Tetrahedron Lett. 1993, 34, 4001–4004.
- 36
- 36aI. P. Holmes, H. B. Kagan, Tetrahedron Lett. 2000, 41, 7453–7456;
- 36bI. P. Holmes, H. B. Kagan, Tetrahedron Lett. 2000, 41, 7457–7460.
- 37
- 37aY. Belokon', N. Ikonnikov, M. Moscalenko, M. North, S. Orlova, V. Tararov, L. Yashkina, Tetrahedron: Asymmetry 1996, 7, 851–855;
- 37bY. Belokon', M. Flego, N. Ikonnikov, M. Moscalenko, M. North, C. Orizu, V. Tararov, M. Tasinazzo, J. Chem. Soc. Perkin Trans. 1 1997, 1293–1295;
- 37cY. N. Belokon', B. Green, N. S. Ikonnikov, M. North, V. I. Tararov, Tetrahedron Lett. 1999, 40, 8147–8150;
- 37dY. N. Belokon', B. Green, N. S. Ikonnikov, M. North, T. Parsons, V. I. Tararov, Tetrahedron 2001, 57, 771–779;
- 37eY. N. Belokon', B. Green, N. S. Ikonnikov, V. S. Larichev, B. V. Lokshin, M. A. Moscalenko, M. North, C. Orizu, A. S. Peregudov, G. I. Timofeeva, Eur. J. Org. Chem. 2000, 2655–2661.
- 38H. Deng, M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2002, 114, 1051–1054; Angew. Chem. Int. Ed. 2002, 41, 1009–1012.
- 39aY. Shen, X. Feng, G. Zhang, Y. Jiang, Synlett 2002, 1353–1355;
- 39bF. Chen, X. Feng, B. Qin, G. Zhang, Y. Jiang, Org. Lett. 2003, 5, 949–952.
- 40
- 40aY. Hamashima, D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 2641–2642;
- 40bY. Hamashima, D. Sawada, H. Nogami, M. Kanai, M. Shibasaki, Tetrahedron 2001, 57, 805–814;
- 40cM. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989–1999, zit. Lit.
- 41
- 41aJ. Casas, C. Nájera, J. M. Sansano, J. M. Saá, Org. Lett. 2002, 4, 2589–2592;
- 41bJ. Casas, A. Baeza, J. M. Sansano, C. Nájera, J. M. Saá, Tetrahedron: Asymmetry 2003, 14, 197–200;
- 41cA. Baeza, J. Casas, C. Nájera, J. M. Sansano, J. M. Saá, Angew. Chem. 2003, 115, 3251–3254; Angew. Chem. Int. Ed. 2003, 42, 3143–3146.
- 42J. Tian, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2002, 114, 3788–3790;
Angew. Chem. Int. Ed. 2002, 41, 3636–3638.
10.1002/1521-3773(20021004)41:19<3636::AID-ANIE3636>3.0.CO;2-B CAS PubMed Web of Science® Google Scholar
- 43
- 43aY. Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 7412–7413;
- 43bK. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9908–9909.
- 44
- 44aM. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6327–6328;
- 44bM. Takamura, K. Funabashi, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 6801–6808;
- 44cK. Funabashi, H. Ratni, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 10 784–10 785.
- 45
- 45aM. Takamura, Y. Hamashima, H. Usuda, M. Kanai, M. Shibasaki, Angew. Chem. 2000, 112, 1716–1718;
10.1002/(SICI)1521-3757(20000502)112:9<1716::AID-ANGE1716>3.0.CO;2-D Google ScholarAngew. Chem. Int. Ed. 2000, 39, 1650–1652;10.1002/(SICI)1521-3773(20000502)39:9<1650::AID-ANIE1650>3.0.CO;2-P CAS PubMed Web of Science® Google Scholar
- 45bM. Takamura, Y. Hamashima, H. Usuda, M. Kanai, M. Shibasaki, Chem. Pharm. Bull. 2000, 48, 1586–1592;
- 45cH. Nogami, S. Matsunaga, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2001, 42, 279–283;
- 45dS. Masumoto, H. Usuda, M. Suzuki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 5634–5635.
- 46M. Chavarot, J. J. Byrne, Y. Chanant, Y. Vallée, Tetrahedron: Asymmetry 2001, 12, 1147–1150.
- 47
- 47aC. A. Krueger, K. W. Kuntz, C. D. Dzierba, W. G. Wirschun, J. D. Gleason, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 1999, 121, 4284–4285;
- 47bJ. R. Porter, W. G. Wirschun, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2000, 122, 2657–2658;
- 47cN. S. Josephsohn, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2001, 123, 11 594–11 599.
- 48
- 48aTetrahedron Organic Chemistry Series, Bd. 9: P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992;
- 48bJ. Christoffers, Eur. J. Org. Chem. 1998, 1259–1266;
10.1002/(SICI)1099-0690(199807)1998:7<1259::AID-EJOC1259>3.0.CO;2-J CAS Web of Science® Google Scholar
- 48cN. Krause, A. Hoffmann-Röder, Synthesis 2001, 171–196;
- 48dJ. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726–1728;
10.1002/ange.200201614 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 1688–1690.
- 49
- 49aH. Sasai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1994, 116, 1571–1572;
- 49bH. Sasai, T. Arai, Y. Satow, K. N. Houk, M. Shibasaki, J. Am. Chem. Soc. 1995, 117, 6194–6198;
- 49cT. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996, 108, 103–105;
10.1002/ange.19961080123 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 104–106;
- 49dM. Shibasaki, H. Sasai, T. Arai, Angew. Chem. 1997, 109, 1290–1310;
10.1002/ange.19971091204 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 1236–1256;
- 49eY. Xu, K. Ohori, T. Ohshima, M. Shibasaki, Tetrahedron 2002, 58, 2585–2588.
- 50E. Keller, N. Veldman, A. L. Spek, B. L. Feringa, Tetrahedron: Asymmetry 1997, 8, 3403–3413.
- 51
- 51aY. S. Kim, S. Matsunaga, J. Das, A. Sekine, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 6506–6507;
- 51bS. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473–8478;
- 51cN. Kumagai, S. Matsunaga, M. Shibasaki, Org. Lett. 2001, 3, 4251–4254;
- 51dR. Takita, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2002, 43, 4661–4665;
- 51eS. Matsunaga, T. Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3–15.
- 52S. Harada, N. Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2582–2590.
- 53S. Matsunaga, T. Ohshima, M. Shibasaki, Tetrahedron Lett. 2000, 41, 8473–8478.
- 54T. Arai, Q.-S. Hu, X.-F. Zheng, L. Pu, H. Sasai, Org. Lett. 2000, 2, 4261–4263.
- 55aG. Manickam, G. Sundararajan, Tetrahedron 1999, 55, 2721–2736;
- 55bG. Sundararajan, N. Prabagaran, Org. Lett. 2001, 3, 389–392.
- 56N. Prabagaran, G. Sundararajan, Tetrahedron: Asymmetry 2002, 13, 1053–1058.
- 57
- 57aE. F. DiMauro, M. C. Kozlowski, Org. Lett. 2001, 3, 1641–1644;
- 57bV. Annamalai, E. F. DiMauro, P. J. Carroll, M. C. Kozlowski, J. Org. Chem. 2003, 68, 1973–1981.
- 58
- 58aJ. K. Myers, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 8959–8960;
- 58bG. M. Sammis, E. N. Jacobsen, J. Am. Chem. Soc. 2003, 125, 4442–4443.
- 59
- 59aK. Itoh, S. Kanemasa, J. Am. Chem. Soc. 2002, 124, 13 394–13 395; siehe auch Kurzaufsatz:
- 59bK. Itoh, S. Kanemasa, Eur. J. Org. Chem., im Druck.
- 60
- 60aJ. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837–838;
- 60bB. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312–3314;
10.1002/(SICI)1521-3757(19981116)110:22<3312::AID-ANGE3312>3.0.CO;2-S Google ScholarAngew. Chem. Int. Ed. 1998, 37, 3124–3126.10.1002/(SICI)1521-3773(19981204)37:22<3124::AID-ANIE3124>3.0.CO;2-1 CAS PubMed Web of Science® Google Scholar
- 61
- 61aA. Yanagisawa, Y. Nakatsuka, K. Asakawa, H. Kageyama, H. Yamamoto, Synlett 2001, 69–72;
- 61bM. Wadamoto, N. Ozasa, A. Yanagisawa, H. Yamamoto, J. Org. Chem. 2003, 68, 5593–5601.
- 62
- 62aS. E. Denmark, R. A. Stavenger, Acc. Chem. Res. 2000, 33, 432–440, zit. Lit.;
- 62bS. E. Denmark, S. K. Ghosh, Angew. Chem. 2001, 113, 4895–4898;
10.1002/1521-3757(20011217)113:24<4895::AID-ANGE4895>3.0.CO;2-1 Google ScholarAngew. Chem. Int. Ed. 2001, 40, 4759–4762.10.1002/1521-3773(20011217)40:24<4759::AID-ANIE4759>3.0.CO;2-G CAS PubMed Web of Science® Google Scholar
- 63H. Sasai, T. Suzuki, S. Arai, T. Arai, M. Shibasaki, J. Am. Chem. Soc. 1992, 114, 4418–4420.
- 64
- 64aY. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942–1944; Angew. Chem. Int. Ed. Engl. 1997, 36, 1871–1873;
- 64bN. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168–4178.
- 65N. Yoshikawa, N. Kumagai, S. Matsunaga, G. Moll, T. Ohshima, T. Suzuki, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2466–2467.
- 66
- 66aN. Kumagai, S. Matsunaga, N. Yoshikawa, T. Ohshima, M. Shibasaki, Org. Lett. 2001, 3, 1539–1542;
- 66bN. Kumagai, S. Matsunaga, T. Kinoshita, S. Harada, S. Okada, S. Sakamoto, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 2169–2178.
- 67
- 67aB. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12 003–12 004;
- 67bB. M. Trost, H. Ito, E. R. Silcoff, J. Am. Chem. Soc. 2001, 123, 3367–3368;
- 67cB. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889–891;
10.1002/1521-3757(20020301)114:5<889::AID-ANGE889>3.0.CO;2-8 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 861–863;10.1002/1521-3773(20020301)41:5<861::AID-ANIE861>3.0.CO;2-V CAS PubMed Web of Science® Google Scholar
- 67dB. M. Trost, V. S. C. Yeh, H. Ito, N. Bremeyer, Org. Lett. 2002, 4, 2621–2623.
- 68
- 68aH. Sasai, M. Hiroi, Y. M. A. Yamada, M. Shibasaki, Tetrahedron Lett. 1997, 38, 6031–6034;
- 68bT. Arai, H. Sasai, K. Aoe, K. Okamura, T. Date, M. Shibasaki, Angew. Chem. 1996 108, 103–105;
10.1002/ange.19961080123 Google ScholarAngew. Chem. Int. Ed. Engl. 1996, 35, 104–106;
- 68cK. Yamada, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 3666–3672.
- 69
- 69aY. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405–6406;
- 69bY. Ito, M. Sawamura, T. Hayashi, Tetrahedron Lett. 1987, 28, 6215–6218;
- 69cY. Ito, M. Sawamura, E. Shirakawa, K. Hayashizaki, T. Hayashi, Tetrahedron Lett. 1988, 29, 235–238;
- 69dM. Sawamura, Y. Ito, T. Hayashi, Tetrahedron Lett. 1990, 31, 2723–2726;
- 69eT. Hayashi, M. Sawamura, Y. Ito, Tetrahedron 1992, 48, 1999–2012. Siehe auch:
- 69fS. D. Pastor, Tetrahedron 1988, 44, 2883–2886;
- 69gS. D. Pastor, A. Togni, J. Am. Chem. Soc. 1989, 111, 2333–2334;
- 69hA. Togni, R. Hausel, Synlett 1990, 633–635;
- 69iS. D. Pastor, A. Togni, Tetrahedron Lett. 1990, 31, 839–840;
- 69jA. Togni, S. D. Pastor, J. Organomet. Chem. 1990, 381, C 21–C25;
- 69kA. Togni, S. D. Pastor, J. Org. Chem. 1990, 55, 1649–1664.
- 70aY. Ito, M. Sawamura, M. Kobayashi, T. Hayashi, Tetrahedron Lett. 1988, 29, 6321–6324;
- 70bY. Ito, M. Sawamura, H. Hamashima, T. Emura, T. Hayashi, Tetrahedron Lett. 1989, 30, 4681–4684;
- 70cM. Sawamura, Y. Ito, T. Hayashi, Tetrahedron Lett. 1989, 30, 2247–2250;
- 70dA. Togni, S. D. Pastor, Tetrahedron Lett. 1989, 30, 1071–1072.
- 71T. Hayashi, Y. Uozumi, A. Yamazaki, M. Sawamura, H. Hamashima, Y. Ito, Tetrahedron Lett. 1991, 32, 2799–2802.
- 72
- 72aK. Yamada, S. J. Harwood, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 3713–3715;
10.1002/(SICI)1521-3757(19991203)111:23<3713::AID-ANGE3713>3.0.CO;2-Z Web of Science® Google ScholarAngew. Chem. Int. Ed. 1999, 38, 3504–3505;10.1002/(SICI)1521-3773(19991203)38:23<3504::AID-ANIE3504>3.0.CO;2-E CAS PubMed Web of Science® Google Scholar
- 72bK. Yamada, G. Moll, M. Shibasaki, Synlett 2001, 980–982;
- 72cN. Tsuritani, K. Yamada, N. Yoshikawa, M. Shibasaki, Chem. Lett. 2002, 276–277.
- 73N. Nishiwaki, K. R. Knudsen, K. V. Gothelf, K. A. Jørgensen, Angew. Chem. 2001 113, 3080–3083;
10.1002/1521-3757(20010817)113:16<3080::AID-ANGE3080>3.0.CO;2-U Google ScholarAngew. Chem. Int. Ed. 2001, 40, 2992–2995.10.1002/1521-3773(20010817)40:16<2992::AID-ANIE2992>3.0.CO;2-3 CAS PubMed Web of Science® Google Scholar
- 74S. Kobayashi, T. Hamada, K. Manabe, J. Am. Chem. Soc. 2002, 124, 5640–5641.
- 75S. Matsunaga, N. Kumagai, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2003, 125, 4712–4713.
- 76B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338–339.
- 77
- 77aI. Paterson, D. J. Berrisford, Angew. Chem. 1992, 104, 1204–1205; Angew. Chem. Int. Ed. Engl. 1992, 31, 1179–1180;
- 77bE. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421–431;
- 77cT. P. Yoon, E. N. Jacobsen, Science 2003, 299, 1691–1693, zit. Lit.
- 78Zu Beispielen der katalytischen asymmetrischen Epoxidierung von Olefinen siehe:
- 78aM. Bougauchi, S. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 2329–2330;
- 78bS. Watanabe, T. Arai, H. Sasai, M. Shibasaki, J. Org. Chem. 1998, 63, 8090–8091;
- 78cT. Nemoto, T. Ohshima, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 2725–2732;
- 78dT. Nemoto, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9474–9475; zu Beispielen der katalytischen asymmetrischen Hydrophosphonylierung und Hydrophosphanierung siehe:
- 78eH. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998, 120, 3089–3103;
- 78fI. Schlemminger, Y. Saida, H. Gröger, W. Maison, N. Durot, H. Sasai, M. Shibasaki, J. Martens, J. Org. Chem. 2000, 65, 4818–4825; zu Beispielen der katalytischen asymmetrischen Ringöffnung von Epoxiden siehe:
- 78gT. Iida, N. Yamamoto, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1997, 119, 4783–4784;
- 78hT. Iida, N. Yamamoto, S. Matsunaga, H. G. Woo, M. Shibasaki, Angew. Chem. 1998, 110, 2383–2386;
10.1002/(SICI)1521-3757(19980817)110:16<2383::AID-ANGE2383>3.0.CO;2-N Google ScholarAngew. Chem. Int. Ed. 1998, 37, 2223–2226;10.1002/(SICI)1521-3773(19980904)37:16<2223::AID-ANIE2223>3.0.CO;2-Z CAS Web of Science® Google Scholar
- 78iS. Matsunaga, J. Das, J. Roels, E. M. Vogl, N. Yamamoto, T. Iida, K. Yamaguchi, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 2252–2260.
- 79
- 79aW. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768–2769;
- 79bW. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1994, 116, 6142–6148;
- 79cB. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656–6666.
- 80
- 80aL. E. Martínez, J. L. Leighton, D. H. Carsten, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5897–5898;
- 80bJ. L. Leighton, E. N. Jacobsen, J. Org. Chem. 1996, 61, 389–390;
- 80cK. B. Hansen, J. L. Leighton, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 10 924–10 925;
- 80dR. G. Konsler, J. Karl, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 10 780–10 781.
- 81aE. N. Jacobsen, F. Kakiuchi, R. G. Konsler, J. F. Larrow, M. Tokunaga, Tetrahedron Lett. 1997, 38, 773–776;
- 81bS. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001–1004.
- 82
- 82aJ. F. Larrow, S. E. Schaus, E. N. Jacobsen, J. Am. Chem. Soc. 1996, 118, 7420–7421;
- 82bH. Lebel, E. N. Jacobsen, Tetrahedron Lett. 1999, 40, 7303–7306.
- 83
- 83aM. Tokunaga, J. F. Larrow, F. Kakiuchi, E. N. Jacobsen, Science 1997, 277, 936–938;
- 83bM. E. Furrow, S. E. Schaus, E. N. Jacobsen, J. Org. Chem. 1998, 63, 6776–6777;
- 83cJ. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 6086–6087;
- 83dS. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307–1315.
- 84
- 84aD. A. Annis, E. N. Jacobsen, J. Am. Chem. Soc. 1999, 121, 4147–4154;
- 84bR. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750–3753;
10.1002/1521-3757(20001016)112:20<3750::AID-ANGE3750>3.0.CO;2-T Google ScholarAngew. Chem. Int. Ed. 2000, 39, 3604–3607;10.1002/1521-3773(20001016)39:20<3604::AID-ANIE3604>3.0.CO;2-9 CAS PubMed Web of Science® Google Scholar
- 84cJ. M. Ready, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 2687–2688;
- 84dJ. M. Ready, E. N. Jacobsen, Angew. Chem. 2002, 114, 1432–1435;
10.1002/1521-3757(20020415)114:8<1432::AID-ANGE1432>3.0.CO;2-6 Google ScholarAngew. Chem. Int. Ed. 2002, 41, 1374–1377;10.1002/1521-3773(20020415)41:8<1374::AID-ANIE1374>3.0.CO;2-8 CAS PubMed Web of Science® Google Scholar
- 84eD. E. White, E. N. Jacobsen, Tetrahedron: Asymmetry 2003, 14, 3633–3638.
- 85M. Sawamura, H. Nagata, Y. Ito, J. Am. Chem. Soc. 1992, 114, 2586–2592.
- 86M. Sawamura, Y. Nakayama, W. M. Tang, Y. Ito, J. Org. Chem. 1996, 61, 9090–9096.
- 87
- 87aS. France, H. Wack, A. M. Hafez, A. E. Taggi, D. R. Witsil, T. Lectka, Org. Lett. 2002, 4, 1603–1605;
- 87bA. E. Taggi, A. M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc. 2002, 124, 6626–6635;
- 87cA. E. Taggi, A. M. Hafez, T. Lectka, Acc. Chem. Res. 2003, 36, 10–19.
- 88A. H. Mermerian, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 4050–4051.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.