Asymmetric Catalysis – Homogeneous
Giambattista Consiglio
Swiss Federal Institute of Technology, Zürich, Switzerland
Search for more papers by this authorGiambattista Consiglio
Swiss Federal Institute of Technology, Zürich, Switzerland
Search for more papers by this authorAbstract
Possible applications of enantioselective catalysis, namely nucleophilic and electrophilic catalyses, as well as of coordination catalysis by transition metal complexes all published before June 2001 are summarized. Enantioface-discriminating and enantiomer-discriminating reactions are considered. The conditions under which enantioselective syntheses occur are briefly described. The most important class of reactions encompasses addition reactions of various addenda to CX double bonds, where X = C, N, and O, whereby either acyclic (e.g., in hydrogenation, hydrosilylation, hydrocarbonylation) or cyclic (e.g., epoxidation, cyclopropanation, Diels–Alder reaction) optically active reaction products are formed. Other reactions involving olefinic substrates, namely isomerization, metathesis, allylic oxidation, the Heck reaction, and conjugated addition, are presented. Furthermore, the Friedel–Crafts and aldol reactions, cross-coupling, the insertion of carbenes into various bonds, the oxidation of CH bonds and sulfides, the Baeyer–Villiger oxidation, and the ring-opening reaction of oxiranes and aziridines are discussed. Some examples of enantioselective polymerization reactions are also given.
Bibliography
- 1 E. L. Eliel, S. H. Wilen, and L. N. Mander, Stereochemistry of Organic Compounds, John Wiley & Sons, Inc., New York, 1994.
- 2 J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, Prentice-Hall, Inc., Englewood Cliffs, N. J., 1971.
- 3 E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Comprehensive Asymmetric Catalysis, Springer, Berlin, 1999.
- 4 G. Quinkert and H. Stark, Angew. Chem., Int. Ed. Engl. 22, 637–655 (1983).
- 5 J. I. Klabunowski, Asymmetrische Synthese, VEB Deutscher Verlag der Wissenschaft, Berlin, 1963.
- 6
H. Pracejus,
Fortschr. Chem. Forsch.
8,
493–553
(1968).
10.1007/BFb0071301 Google Scholar
- 7 G. Natta, L. Porri, and S. Valenti, Makromol. Chem. 67, 225–228 (1963).
- 8
I. Ojima,
Catalytic Asymmetric Synthesis,
Wiley-VHC,
New York,
2000.
10.1002/0471721506 Google Scholar
- 9 K. Mikami and co-workers, Angew. Chem., Int. Ed. 38, 3532–3556 (2000).
- 10 D. G. Blackmond, Acc. Chem. Res. 33, 402–411 (2000).
- 11 K. Soai, S. Takanori, and I. Sato, Acc. Chem. Res. 33, 382–390 (2000).
- 12 G. Helmchen, in G. Helmchen, R. W. Hoffmann, J. Mulzer, and E. Schaumann, eds., Methods of Organic Chemistry (Houben-Weyl), Gerg Thieme Verlag, Stuttgart, 1995, Vol. E 21a, pp. 1–74.
- 13 V. Prelog and G. Helmchen, Angew. Chem., Int. Ed. Engl. 21, 567–583 (1982).
- 14 H. B. Kagan and J. C. Fiaud, Top. Stereochem. 18, 249–330 (1988).
- 15 H. Buschmann, H.-D. Scharf, N. Hoffmann, and P. Esser, Angew. Chem., Int. Ed. Engl. 30, 477–491 (1991).
- 16 G. Helmchen and A. Pfaltz, Acc. Chem. Res. 33, 336–345 (2000).
- 17 M. V. Troutmam, D. H. Appella, and S. L. Buchwald, J. Am. Chem. Soc. 121, 4916–4917 (1999).
- 18 T. Yamada and co-workers, Inorg. Chim. Acta 296, 86–93 (1999).
- 19 R. Giernoth and co-workers, J. Am. Chem. Soc. 122, 12381–12382 (2000).
- 20 J. A. Wiles and S. H. Bergens, Organometallics 18, 3709–3714 (1999).
- 21 I. D. Gridnev and co-workers, J. Am. Chem. Soc. 122, 7183–7194 (2000).
- 22
Q. Jiang and co-workers,
Angew. Chem., Int. Ed.
37,
1100–1103
(1998).
10.1002/(SICI)1521-3773(19980504)37:8<1100::AID-ANIE1100>3.0.CO;2-3 CAS PubMed Web of Science® Google Scholar
- 23 C. Girard, J.-P. Genêt, and M. Bulliard, Eur. J. Org. Chem. 2937–2942 (1999).
- 24 P. J. Pye and co-workers, Tetrahedron Lett. 39, 4441–4444 (1998).
- 25 Z. Zhang and co-workers, J. Org. Chem. 65, 6223–6226 (2000).
- 26 M. J. Palmer and M. Wills, Tetrahedron: Asymmetry 10, 2045–2061 (1999).
- 27 J. A. Kenny and co-workers, Chem. Commun. 99–100 (2000).
- 28 J. Mao and D. C. Baker, Org. Lett. 1, 841–843 (2000).
- 29 G. Pioda and A. Togni, Tetrahedron: Asymmetry 9, 3903–3910 (1998).
- 30 P.-F. Fu and co-workers, J. Am. Chem. Soc. 117, 7157–7168 (1995).
- 31 R. Kuwano and co-workers, Bull. Chem. Soc. Jpn. 73, 485–486 (2000).
- 32 M. C. Hansen and S. L. Buchwald, Org. Lett. 2, 713–715 (2000).
- 33 H. Jockel and co-workers, Angew. Chem., Int. Ed. 40, 40–73 (2000).
- 34
E. J. Corey and
C. J. Helal,
Angew. Chem., Int. Ed.
37,
1986–2012
(1998).
10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO;2-Z CAS PubMed Web of Science® Google Scholar
- 35 J. M. Brunel, O. Legrand, and G. Buono, Eur. J. Org. Chem. 3313–3321 (2000).
- 36 Y. Ohtsuka and co-workers, Synlett 535–537 (2000).
- 37 M. Lautens and co-workers, Pure Appl. Chem. 70, 1059–1065 (1998).
- 38
S. Breeden and co-workers,
Angew. Chem., Int. Ed.
39,
4106–4108
(2000).
10.1002/1521-3773(20001117)39:22<4106::AID-ANIE4106>3.0.CO;2-L CAS PubMed Web of Science® Google Scholar
- 39 M. Imai, M. Tanaka, and H. Suemune, Tetrahedron 57, 1205–1211 (2001).
- 40 P. Cao and X. Zhang, J. Am. Chem. Soc. 121, 7708–7709 (1999).
- 41 T. Ooi and co-workers, Synlett 1133–1134 (2000).
- 42 J.-S. You, H.-M. Gau, and M. C. K. Choi, Chem. Commun. 1963–1964 (2000).
- 43 Y. N. Belokon, M. North, and T. Parsons, Org. Lett. 2, 1617–1619 (2000).
- 44 L. Z. Flores-Lopéz and co-workers, Organometallics 19, 2153–2160 (2000).
- 45 Y. Hamashima, M. Kanai, and M. Shibasaki, J. Am. Chem. Soc. 122, 7412–7413 (2000).
- 46 P. Vachal and E. N. Jacobsen, Org. Lett. 2, 867–870 (2000).
- 47 H. Ishitani and co-workers, J. Am. Chem. Soc. 122, 762–766 (2000).
- 48 N. S. Perch, T. Pei, and R. A. Widenhoefer, J. Org. Chem. 65, 3836–3845 (2000).
- 49
P. Cao and
X. Zhang,
Angew. Chem., Int. Ed.
39,
4104–4106
(2000).
10.1002/1521-3773(20001117)39:22<4104::AID-ANIE4104>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 50 R. Aufdenblatten, S. Diezi, and A. Togni, Monatsh. Chem. 131, 1345–1350 (2000).
- 51 C. Döbler and co-workers, J. Am. Chem. Soc. 122, 10289–10297 (2000).
- 52
P. O'Brien,
Angew. Chem., Int. Ed.
38,
326–329
(1999).
10.1002/(SICI)1521-3773(19990201)38:3<326::AID-ANIE326>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 53 P. Wipf and S. Ribe, Org. Lett. 2, 1713–1716 (2000).
- 54 N. Nakamura, A. Hirai, and E. Nakamura, J. Am. Chem. Soc. 122, 978–979 (2000).
- 55 L. Pu and H.-B. Yu, Chem. Rev. 101, 757–824 (2001).
- 56 N. Arroyo and co-workers, Tetrahedron: Asymmetry 11, 4207–4219 (2000).
- 57 J. R. Porter and co-workers, J. Am. Chem. Soc. 123, 984–985 (2001).
- 58
T. Gastner and co-workers,
Angew. Chem., Int. Ed.
40,
1896–1898
(2001).
10.1002/1521-3773(20010518)40:10<1896::AID-ANIE1896>3.0.CO;2-W CAS PubMed Web of Science® Google Scholar
- 59 M. Kameyama and N. Kamigata, Bull. Chem. Soc. Jpn. 62, 648–650 (1989).
- 60 A. M. Daly, M. F. Renehan, and D. G. Gilheany, Org. Lett. 3, 663–666 (2001).
- 61 M. Frohn and Y. Shi, Synthesis 1979–2000 (2000).
- 62 H. Tian, X. She, and Y. Shi, Org. Lett. 3, 715–718 (2001).
- 63 J. R. Porter and J. Skidmore, Chem. Commun. 1215–1225 (2000).
- 64
E. M. Vogl,
H. Gröger and
M. Shibasaki,
Angew. Chem., Int. Ed.
38,
1570–1577
(1999).
10.1002/(SICI)1521-3773(19990601)38:11<1570::AID-ANIE1570>3.0.CO;2-Y CAS PubMed Web of Science® Google Scholar
- 65 P. Brandt and co-workers, J. Am. Chem. Soc. 122, 8013–8020 (2000).
- 66
J. C. Antilla and
W. D. Wulff,
Angew. Chem., Int. Ed.
39,
4518–4521
(2000).
10.1002/1521-3773(20001215)39:24<4518::AID-ANIE4518>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- 67 T. Niimi and co-workers, Adv. Synth. Catal. 343, 79–88 (2001).
- 68 K. V. Gothelf and K. A. Jørgensen, Chem. Rev. 98, 863–910 (1998).
- 69 K. Hiroi and co-workers, Tetrahedron: Asymmetry 11, 797–808 (2000).
- 70 N. Jeong, B. K. Sung, and Y. K. Choi, J. Am. Chem. Soc. 122, 6771–6772 (2000).
- 71 T. Shibata and K. Takagi, J. Am. Chem. Soc. 122, 9852–9853 (2000).
- 72
K. A. Jørgensen,
Angew. Chem., Int. Ed.
39,
3558–3588
(2000).
10.1002/1521-3773(20001016)39:20<3558::AID-ANIE3558>3.0.CO;2-I CAS PubMed Web of Science® Google Scholar
- 73 K. Aikawa, R. Irie, and T. Katsuki, Tetrahedron Lett. 57, 845–851 (2001).
- 74 M. P. Doyle, I. M. Phillips, and W. Hu, J. Am. Chem. Soc. 123, 1778–1779 (2001).
- 75 A. Bayer and O. R. Gautun, Tetrahedron Lett. 41, 3743–3746 (2000).
- 76 C. Chapuis, M. Barthe, and J.-Y. de Saint Laumer, Helv. Chim. Acta 84, 230–242 (2001).
- 77 K. Tanaka and co-workers, J. Am. Chem. Soc. 122, 9870–9871 (2000).
- 78
H. Frauenrath and co-workers,
Angew. Chem., Int. Ed.
40,
177–179
(2001).
10.1002/1521-3773(20010105)40:1<177::AID-ANIE177>3.0.CO;2-X CAS PubMed Web of Science® Google Scholar
- 79
A. H. Hoveyda and
R. R. Schrock,
Chem. Eur. J.
7,
945–950
(2001).
10.1002/1521-3765(20010302)7:5<945::AID-CHEM945>3.0.CO;2-3 CAS PubMed Web of Science® Google Scholar
- 80 H. Nakano and co-workers, J. Org. Chem. 66, 620–625 (2001).
- 81 T. Mino and co-workers, J. Org. Chem. 66, 1795–1797 (2001).
- 82 H. Kodama and co-workers, Tetrahedron: Asymmetry 11, 4009–4015 (2000).
- 83 A. Saitoh, T. Uda, and T. Morimoto, Tetrahedron: Asymmetry 11, 4049–4053 (2000).
- 84 J. Clayden and co-workers, J. Org. Chem. 65, 7033–7040 (2000).
- 85 K. Fuji and co-workers, Synlett 351–352 (2000).
- 86 M. Kawatsura and co-workers, Tetrahedron 56, 2247–2257 (2000).
- 87 M. Shibasaki and E. M. Vogl, J. Organomet. Chem. 576, 1–15 (1999).
- 88 O. Loiseleur and co-workers, J. Organomet. Chem. 576, 16–22 (1999).
- 89 S. J. Degrado, H. Mizutani, and A. H. Hoveyda, J. Am. Chem. Soc. 123, 755–756 (2001).
- 90 T. Hayashi, T. Senda, and M. Ogasawara, J. Am. Chem. Soc. 122, 10716–10717 (2000).
- 91 Y. Moritani and co-workers, J. Am. Chem. Soc. 122, 6797–6798 (2000).
- 92 D. A. Evans and co-workers, J. Am. Chem. Soc. 122, 7936–7943 (2000).
- 93 W. J. Drury III and co-workers, J. Am. Chem. Soc. 120, 11006–11007 (1998).
- 94 S. Yao, X. Fang, and K. A. Jørgensen, Chem. Commun. 2547–2548 (1998).
- 95 N. Gathergood, W. Zhuang, and K. A. Jørgensen, J. Am. Chem. Soc. 122, 12517–12522 (2000).
- 96
K. B. Jensen and co-workers,
Angew. Chem., Int. Ed.
40,
160–163
(2001).
10.1002/1521-3773(20010105)40:1<160::AID-ANIE160>3.0.CO;2-S CAS PubMed Web of Science® Google Scholar
- 97 J. Yin and S. L. Buchwald, J. Am. Chem. Soc. 122, 12051–12052 (2000).
- 98 A. N. Cammidge and K. V. L. Crépy, Chem. Commun. 1723–1724 (2000).
- 99 X. Li, J. Yang, and M. C. Kozlowski, Org. Lett. 3, 1137–1140 (2001).
- 100
T. D. Machajewski and
C.-H. Wong,
Angew. Chem., Int. Ed.
39,
1352–1374
(2000).
10.1002/(SICI)1521-3773(20000417)39:8<1352::AID-ANIE1352>3.0.CO;2-J CAS PubMed Web of Science® Google Scholar
- 101 S. E. Denmark and R. A. Stavenger, Acc. Chem. Res. 33, 432–440 (2000).
- 102 W. Notz and B. List, J. Am. Chem. Soc. 122, 7386–7387 (2000).
- 103 N. Yoshikawa and co-workers, J. Am. Chem. Soc. 123, 2466–2467 (2001).
- 104 B. M. Trost, H. Ito, and E. R. Silcoff, J. Am. Chem. Soc. 123, 3367–3368 (2001).
- 105 H. M. L. Davies and E. G. Antoulinakis, J. Organomet. Chem. 617–618, 47–55 (2000).
- 106 D. M. Hodgson, F. Y. T. M. Pierard, and P. A. Stupple, Chem. Soc. Rev. 30, 50–61 (2001).
- 107 M. A. M. Capozzi and co-workers, J. Am. Chem. Soc. 121, 4708–4709 (1999).
- 108 C. Paneghetti and co-workers, Organometallics 18, 5057–5065 (1999).
- 109 B. Tao, M. M.-C. Lo, and G. C. Fu, J. Am. Chem. Soc. 123, 353–354 (2001).
- 110 X. Feng, L. Shu, and Y. Shi, J. Am. Chem. Soc. 121, 11002–11003 (1999).
- 111 P. Müller and P. Nury, Org. Lett. 1, 439–441 (1999).
- 112 Z. Li, M. Fernández, and E. N. Jacobsen, Org. Lett. 1, 1611–1613 (1999).
- 113 Y. Ito and co-workers, J. Am. Chem. Soc. 120, 11880–11893 (1998).
- 114 K. Nozaki, K. Nakano, and T. Hiyama, J. Am. Chem. Soc. 121, 11008–11009 (1999).
- 115 I. Schlemminger and co-workers, J. Org. Chem. 65, 4818–4825 (2000).
- 116 B. L. Hodous, J. C. Ruble, and G. C. Fu, J. Am. Chem. Soc. 121, 2637–2638 (1999).
- 117
S. Arai,
S. Bellemin-Laponnaz, and
G. C. Fu,
Angew. Chem., Int. Ed.
40,
234–236
(2001).
10.1002/1521-3773(20010105)40:1<234::AID-ANIE234>3.0.CO;2-K CAS PubMed Web of Science® Google Scholar
- 118 L. Hintermann and A. Togni, Helv. Chim. Acta 83, 2425–2435 (2000).
- 119 Y. Uozumi and co-workers, J. Org. Chem. 64, 1620–1625 (1999).
- 120 M. Lautens and co-workers, J. Am. Chem. Soc. 117, 6863–6879 (1995).
- 121 J. Åhman and co-workers, J. Am. Chem. Soc. 120, 1918–1919 (1998).
- 122 M. Takamura and co-workers, J. Am. Chem. Soc. 122, 6237–6238 (2000).
- 123 M. P. Sibi and N. A. Porter, Acc. Chem. Res. 32, 163–171 (1999).
- 124 H.-J. Knölker, Chem. Rev. 100, 2941–2961 (2000).
- 125 B. Gotov and H.-G. Schmalz, Org. Lett. 3, 1753–1756 (2001).