Iridium-Catalyzed anti-Diastereo- and Enantioselective Carbonyl (α-Trifluoromethyl)allylation from the Alcohol or Aldehyde Oxidation Level†
Xin Gao
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
Search for more papers by this authorDr. Yong Jian Zhang
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
Search for more papers by this authorCorresponding Author
Prof. Michael J. Krische
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696Search for more papers by this authorXin Gao
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
Search for more papers by this authorDr. Yong Jian Zhang
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
Search for more papers by this authorCorresponding Author
Prof. Michael J. Krische
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696
University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station–A5300, Austin, TX 78712-1167 (USA), Fax: (+1) 512-471-8696Search for more papers by this authorAcknowledgements is made to the Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1-GM069445). Y.J.Z. acknowledges partial financial support from Shanghai Jiao Tong University.
Graphical Abstract
Florierendes Fluor: Die Umsetzung eines α-Trifluormethylallylbenzoats mit Alkoholen in Gegenwart eines ortho-cyclometallierten Iridium-Katalysators führt zur Bildung von Aldehyd-Allyliridium-Intermediaten, aus denen die enantiomerenangereicherten Produkte einer anti-α-Trifluormethylallylierung entstehen. Ein identischer Satz von Produkten wird ausgehend von Aldehyden erhalten, wenn ähnliche Transferhydrierungsbedingungen mit Isopropylalkohol als terminalem Reduktionsmittel angewendet werden.
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References
- 1aA. M. Thayer, Chem. Eng. News 2006, 84, 15–24;
- 1bK. Mueller, C. Faeh, F. Diederich, Science 2007, 317, 1881–1886;
- 1cA. M. Thayer, Chem. Eng. News 2007, 85, 11–19.
- 2
- 2aJ. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337–2347;
- 2bV. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song, Chem. Rev. 2006, 106, 2734–2793.
- 3For reviews on enantioselective fluorination, see:
- 3aJ.-A. Ma, D. Cahard, Chem. Rev. 2004, 104, 6119–6146;
- 3bV. A. Brunet, D. O’Hagan, Angew. Chem. 2008, 120, 1198–1201;
10.1002/ange.200704700 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1179–1182;
- 3cC. Bobbio, V. Gouverneur, Org. Biomol. Chem. 2006, 4, 2065–2075;
- 3dC. Audouard, J.-A. Ma, D. Cahard, Adv. Org. Synth. 2006, 2, 431–461;
- 3eJ.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1–PR43;
- 3fL.-L. Cao, B. L. Gao, S.-T. Ma, Z.-P. Liu, Curr. Org. Chem. 2010, 14, 889–916;
- 3gY. Ku Kang, D. Y. Kim, Curr. Org. Chem. 2010, 14, 917–927;
- 3hD. Cahard, X. Xu, S. Couve-Bonnaire, X. Pannecoucke, Chem. Soc. Rev. 2010, 39, 558–568.
- 4For reviews on enantioselective trifluoromethylation, see:
- 4aJ.-A. Ma, D. Cahard, J. Fluorine Chem. 2007, 128, 975–996;
- 4bT. Billard, B. R. Langlois, Eur. J. Org. Chem. 2007, 891–897;
- 4cN. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry 2008, 19, 2633–2644;
- 4dJ. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455–529, and reference [3a].
- 5For aldehyde (trifluoromethyl)allylation and related processes, see:
- 5aT. Yamazaki, N. Ishikawa, Chem. Lett. 1984, 521–524;
- 5bY. Hanzawa, S. Ishizawa, Y. Kobayashi, T. Taguchi, Chem. Pharm. Bull. 1990, 38, 1104–1106;
- 5cT.-P. Loh, X.-R. Li, Angew. Chem. 1997, 109, 1029–1031; Angew. Chem. Int. Ed. Engl. 1997, 36, 980–982;
- 5dT.-P. Loh, X.-R. Li, Tetrahedron Lett. 1997, 38, 869–872;
- 5eT.-P. Loh, X.-R. Li, Eur. J. Org. Chem. 1999, 1893–1899;
10.1002/(SICI)1099-0690(199908)1999:8<1893::AID-EJOC1893>3.0.CO;2-3 CAS Web of Science® Google Scholar
- 5fT. Sakamoto, K. Takahashi, T. Yamazaki, T. Kitazume, J. Org. Chem. 1999, 64, 9467–9474;
- 5gQ. Chen, X.-L. Qiu, F.-L. Qing, J. Org. Chem. 2006, 71, 3762–3767.
- 6For selected reviews on enantioselective carbonyl allylation and crotylation, see:
- 6aR. W. Hoffmann, Angew. Chem. 1982, 94, 569–580; Angew. Chem. Int. Ed. Engl. 1982, 21, 555–566;
- 6bY. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207–2293;
- 6cP. V. Ramachandran, Aldrichimica Acta 2002, 35, 23–35;
- 6dJ. W. J. Kennedy, D. G. Hall, Angew. Chem. 2003, 115, 4880–4887; Angew. Chem. Int. Ed. 2003, 42, 4732–4739;
- 6eS. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763–2793;
- 6fC.-M. Yu, J. Youn, H.-K. Jung, Bull. Korean Chem. Soc. 2006, 27, 463–472;
- 6gI. Marek, G. Sklute, Chem. Commun. 2007, 1683–1691;
- 6hD. G. Hall, Synlett 2007, 1644–1655.
- 7For selected reviews on CC bond-forming transfer hydrogenation, see:
- 7aR. L. Patman, J. F. Bower, I. S. Kim, M. J. Krische, Aldrichimica Acta 2008, 41, 95–104;
- 7bF. Shibahara, M. J. Krische, Chem. Lett. 2008, 37, 1102–1107;
- 7cJ. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische, Angew. Chem. 2009, 121, 36–48; Angew. Chem. Int. Ed. 2009, 48, 34–46;
- 7dS. B. Han, I. S. Kim, M. J. Krische, Chem. Commun. 2009, 7278–7287.
- 8For enantioselective carbonyl allylation by iridium catalyzed CC bond-forming transfer hydrogenation and related processes, see:
- 8aI. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 6340–6341;
- 8bI. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14891–14899;
- 8cI. S. Kim, S.-B. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 2514–2520;
- 8dS. B. Han, I.-S. Kim, H. Han, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 6916–6917;
- 8eY. Lu, I.-S. Kim, A. Hassan, D. J. Del Valle, M. J. Krische, Angew. Chem. 2009, 121, 5118–5121; Angew. Chem. Int. Ed. 2009, 48, 5018–5021;
- 8fJ. Itoh, S. B. Han, M. J. Krische, Angew. Chem. 2009, 121, 6431–6434; Angew. Chem. Int. Ed. 2009, 48, 6313–6316;
- 8gY. Lu, M. J. Krische, Org. Lett. 2009, 11, 3108–3111;
- 8hA. Hassan, Y. Lu, M. J. Krische, Org. Lett. 2009, 11, 3112–3115;
- 8iB. Bechem, R. L. Patman, S. Hashmi, M. J. Krische, J. Org. Chem. 2010, 75, 1795–1798;
- 8jS. B. Han, H. Han, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 1760–1761;
- 8kY. J. Zhang, J. H. Yang, S. H. Kim, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 4562–4563;
- 8lS. B. Han, X. Gao, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 9153–9156;
- 8mJ. R. Zbieg, T. Fukuzumi, M. J. Krische, Adv. Synth. Catal. 2010, 352, 2416–2420.
- 9For selected examples of catalyst-directed diastereoselectivity, see:
- 9aN. Minami, S. S. Ko, Y. Kishi, J. Am. Chem. Soc. 1982, 104, 1109–1111;
- 9bS. Y. Ko, A. W. M. Lee, S. Masamune, L. A. Reed III, K. B. Sharpless, F. J. Walker, Science 1983, 220, 949–951;
- 9cS. Kobayashi, A. Ohtsubo, T. Mukaiyama, Chem. Lett. 1991, 831–834;
- 9dA. Hammadi, J. M. Nuzillard, J. C. Poulin, H. B. Kagan, Tetrahedron: Asymmetry 1992, 3, 1247–1262;
- 9eM. P. Doyle, A. V. Kalinin, D. G. Ene, J. Am. Chem. Soc. 1996, 118, 8837–8846;
- 9fB. M. Trost, T. L. Calkins, C. Oertelt, J. Zambrano, Tetrahedron Lett. 1998, 39, 1713–1716;
- 9gE. P. Balskus, E. N. Jacobsen, Science 2007, 317, 1736–1740;
- 9hS. B. Han, J. R. Kong, M. J. Krische, Org. Lett. 2008, 10, 4133–4135.
- 10O. K. Karjalainen, M. Passiniemi, A. M. P. Koskinen, Org. Lett. 2010, 12, 1145–1147.
- 11Q. Chen, F.-L. Qing, Tetrahedron 2007, 63, 11965–11972.
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