Intramolecular s(N)2 reaction α- to a trifluoromethyl group: Preparation of 1-cyano-2-trifluoromethylcyclopropane

Tetrahedron Asymmetry

Volumn 10, Issue 13, 1999, Pages 2583-2589

  Katagiri, Toshimasa ^a   Irie, Minoru ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; CARBON; CYCLOPROPANE DERIVATIVE; METHYL GROUP; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033516436     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00253-0     Document Type: Article

References (31)

1. 1. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedicinal Targets; Soloshonok, V, A., Ed.; Wiley: Chichester, 1999.
2. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
3. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
4. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
5. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
6. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
7. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
8. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
9. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
10. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
11. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
12. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
13. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
14. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
15. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
16. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
17. 2. For a recent review see: Iseki, K. Tetrahedron 1998, 54, 13887-13914. The optically active α-trifluoromethylated alcohols have been prepared by a diastereomeric separation with a chiral amine: von dem Bussche-Hunnefeld, C; Cescato, C.; Seebach, D. Chem. Ber. 1992, 125, 2795-2802; a lipase-promoted enantioselective acylation: Hamada, H.; Shiromoto, M.; Funahashi, M.; Itoh, T.; Nakamura, K. J. Org. Chem. 1996, 61, 2332-2336; lipase-promoted enantioselective deacylations: Shimizu, M.; Sugiyama, K.; Fujisawa, T. Bull. Chem. Soc. Jpn. 1996, 69, 2655-2659; Itoh, T.; Shiromoto, M.; Inoue, H.; Hamada, H.; Nakamura, K. Tetrahedron Lett. 1996, 37, 5001-5002; an enzymatic reduction of ketones: Nakamura, K.; Matsuda, T.; Itoh, T.; Ohno, A. Tetrahedron Lett. 1996, 37, 5727-5730; microbial reductions of ketones: Fujisawa, T.; Onogawa, Y.; Sato, A.; Mitsuya, T.; Shimizu, M. Tetrahedron 1998, 54, 4267-4276; Amone, A.; Bernardi, R.; Blasco, F.; Cardillo, R.; Resnati, G.; Gerus, I. I.; Kukhar, V. P. Tetrahedron 1998, 54, 2809-2818; Nakamura, K.; Matsuda, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1998, 54, 8393-8402; ring opening reactions of optically active 3,3,3-trifluoropropene oxide, for a recent review see Ref. 1, Chapter 5, pp. 161-178; asymmetric reductions of ketones: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387; Ramachandran, P. V.; Gong, B.; Brown, H. C. J. Org. Chem. 1995, 60, 41-46; the Sharpless asymmetric dihydroxylation of trifluoromethylated olefins: Vanhessche, K. P. M.; Sharpless, K. B. Chem. Eur. J. 1997, 3, 517-522; an asymmetric ene reaction: Mikami, K.; Yajima, T.; Terada, M.; Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087-1090; and asymmetric aldol condensations: Soloshonok, V. A.; Avilov D. V.; Kukhar, V. P. Tetrahedron: Asymmetry 1996, 7, 1547-1550; Fernandez, R.; Martin-Zamora, E.; Pareja, C.; Vazquez, J.; Diez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3428-3430.
18. 3. Shinohara, N.; Yamazaki, T.; Kitazume, T. Rev. Heteroatom Chem. 1996, 14, 165-182.
19. 4. Bonnet-Delpon, D.; Cambillau, C.; Charpentier-Morize, M.; Jacquot, R.; Mesureur, D.; Ourevitch, M. J. Org. Chem. 1988, 53, 754-759.
20. 5. Uneyama, K.; Momota, M. Tetrahedron Lett. 1989, 30, 2265-2266.
21. 6. Katayama, M.; Kimoto, H.; Gautam, R. K.; Nishida, M.; Fujii, S. Report. Gov. Indust. Res. Inst. Nagoya 1992, 41, 185-195.
22. 7. Tsushima, T.; Kawada, K.; Ishihara, S.; Uchida, N.; Shiratori, O.; Higaki, J.; Hirata, M. Tetrahedron 1988, 44, 5375-5387.
23. 8. Kubota, T.; Kato, K.; Katagiri, T. Jpn. Kokai Tokkyo Koho 1993, JP 05-178778.
24. 9. Sattler, A.; Haufe, G. Tetrahedron 1996, 52, 5469-5474.
25. 10. 1,1,1-Trifluoro-2-propanol has been estimated to have 0.013 Å shorter C-O bond than non-fluorinated 2-propanol (1.397 Å for 1,1,1-trifluoro-2-propanol and 1.410 Å for 2-propanol) by PM3 geometry optimization using MacSpartan Plus.
26. N2 reaction by nitrogen nucleophiles; Katagiri, T.; Ihara, H.; Takahashi, M.; Kashino, S.; Furuhashi, K.; Uneyama, K. Tetrahedron: Asymmetry 1997, 8, 2933-2937.
27. 12. The optically active (S)-3,3,3-trifluoropropene oxide (75% ee) is commercially available from Japan Energy Corporation.
28. 13. Katagiri, T.; Akizuki, M.; Kuriyama, T.; Shinke, S.; Uneyama, K. Chem. Lett. 1997, 549-550.
29. 14. Semiempirical molecular orbital calculation (PM3) of the two diastereomeric products showed that the difference in energy between two diastereomers is only 0.1 kcal/mol. Thus, the present cyclization would be a kinetic stereocontrolled process.
30. 3 and phenyl groups would have a trans relationship.
31. 16. Major product (>70%) of this reaction was 4-cyano-1,1,1-trifluoro-2-butyl tosylate, tosyl ester of the starting compound, together with small amounts (<5%) of compounds of undefined structure.