Highly enantio- and diastereoselective synthesis of 2-substituted 1-bicyclo[3.1.0]hexanols

Angewandte Chemie - International Edition

Volumn 37, Issue 19, 1998, Pages 2666-2668

  Mizojiri, Ryo ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Cyclizations; Cyclopropanols; Titanium

Indexed keywords

EID: 0032538466     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K     Document Type: Article

References (39)

1. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
2. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
3. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
4. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
5. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
6. Reviews: S. Murai, I. Ryu, N. Sonoda, J. Organometal. Chem. 1983, 250, 121-133; I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1-39; I. Kuwajima, E. Nakamura in Comprehensive Organic SynΣ thesis, Vol. 7 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 441-454; T. Hirao, Top. Curr. Chem. 1996, 178, 99-147; other reports: I. Ryu, K. Matsumoto, Y. Kameyama, M. Ando, N. Kusumoto, A. Ogawa, N. Kambe, S. Murai, N. Sonoda, J. Am. Chem. Soc. 1993, 115, 12330-12339; M. Kirihara, S. Yokoyama, H. Kakuda, T. Momose, Tetrahedron Lett. 1995, 36, 6907-6910, and references therein.
7. For the preparation of optically active, bicyclic cyclopropanols, see T. Sugimura, T. Futagawa, A. Tai, Tetrahedron Lett. 1988, 29, 5775-5778; T. Sugimura, T. Futagawa, M. Yoshikawa, A. Tai, Tetrahedron Lett. 1989, 30, 3807-3810.
8. For the preparation of optically active, bicyclic cyclopropanols, see T. Sugimura, T. Futagawa, A. Tai, Tetrahedron Lett. 1988, 29, 5775-5778; T. Sugimura, T. Futagawa, M. Yoshikawa, A. Tai, Tetrahedron Lett. 1989, 30, 3807-3810.
9. For the preparation of other types of optically active cyclopropanols, see T. Kunz, H.-U. Reissing, Tetrehedron Lett. 1989, 30, 2079-2082; T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979.
10. For the preparation of other types of optically active cyclopropanols, see T. Kunz, H.-U. Reissing, Tetrehedron Lett. 1989, 30, 2079-2082; T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979.
11. For the preparation of other types of optically active cyclopropanols, see T. Kunz, H.-U. Reissing, Tetrehedron Lett. 1989, 30, 2079-2082; T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988; J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979.
12. a) A. Kasatkin, F. Sato, Tetrahedron Lett. 1995, 36, 6079-6082;
13. b) A. Kasatkin, K. Kobayashi, S. Okamoto, F. Sato, Tetrahedron Lett. 1996, 37, 1849-1852;
14. c) J. Lee, H. Kim, J. K. Cha, J. Am. Chem. Soc. 1996, 118, 4198-4199;
15. d) J. Lee, Y. G. Kim, J. G. Bae, J. K. Cha, J. Org. Chem. 1996, 61, 4878-4879;
16. e) S. Okamoto, M. Iwakubo, K. Kobayashi, F. Sato. J. Am. Chem. Soc. 1997, 119, 6984-6990;
17. f) J. S. U, J. Lee, J. K. Cha, Tetrahedron Lett. 1997, 38, 5233-5236;
18. g) S. Hikichi, G. P.-J. Hareau, F. Sato, Tetrahedron Lett. 1997, 38, 8299-8302.
19. V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492; Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414; J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585; V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114; J. Lee, J. S. U, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 10241-10242.
20. V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492; Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414; J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585; V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114; J. Lee, J. S. U, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 10241-10242.
21. V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492; Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414; J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585; V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114; J. Lee, J. S. U, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 10241-10242.
22. V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492; Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414; J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585; V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114; J. Lee, J. S. U, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 10241-10242.
23. V. Chaplinski, A. de Meijere, Angew. Chem. 1996, 108, 491-492; Angew. Chem. Int. Ed. Engl. 1996, 35, 413-414; J. Lee, J. K. Cha, J. Org. Chem. 1997, 62, 1584-1585; V. Chaplinski, H. Winsel, M. Kordes, A. de Meijere, Synlett 1997, 111-114; J. Lee, J. S. U, S. C. Blackstock, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 10241-10242.
24. J. Lee, J. D. Ha, J. K. Cha, J. Am. Chem. Soc. 1997, 119, 8127-8128.
25. S. Y. Cho, J. Lee, R. K. Rammi, J. K. Cha, J. Org. Chem. 1997, 62, 8235-8236.
26. O. G. Kulinkovich, S. V. Sviridov, D. A. Vasilevski, Synthesis 1991, 234.
27. E. J. Corey, A. Rao, M. C. Noe, J. Am. Chem. Soc. 1994, 116, 9345-9346.
28. Reviews: W. Oppolzer, Pure Appl. Chem. 1990, 62, 1241-1250; B. H. Kim, D. P. Curran, Tetrahedron 1993, 49, 293-318.
29. Reviews: W. Oppolzer, Pure Appl. Chem. 1990, 62, 1241-1250; B. H. Kim, D. P. Curran, Tetrahedron 1993, 49, 293-318.
30. W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 5603-5606; W. Oppolzer, J. Blagg, I. Rodriguez, E. Walter, J. Am. Chem. Soc. 1990, 112, 2767-2772.
31. W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 5603-5606; W. Oppolzer, J. Blagg, I. Rodriguez, E. Walter, J. Am. Chem. Soc. 1990, 112, 2767-2772.
32. To the best of our knowledge, asymmetric induction by nucleophilic addition to the carbonyl group of the acylcamphorsultams has not been reported.
33. A. I. Meyers, D. R. Williams, M. Druelinger, J. Am. Chem. Soc. 1976, 98, 3032-3033; K. Saigo, A. Kasahara, S. Ogawa, H. Nohira, Tetrahedron Lett. 1983, 24, 511-512.
34. A. I. Meyers, D. R. Williams, M. Druelinger, J. Am. Chem. Soc. 1976, 98, 3032-3033; K. Saigo, A. Kasahara, S. Ogawa, H. Nohira, Tetrahedron Lett. 1983, 24, 511-512.
35. Y. Ito, S. Fujii, M. Nakatsuka, F. Kawamoto, T. Saegusa in Organic Syntheses, Coll. Vol. 6 (Ed.: W. E. Noland), Wiley, New York, 1988, pp. 327-333.
36. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875; D. A. Evans, E. Vogel, J. V. Nelson, J. Am. Chem. Soc. 1979, 101, 6120-6123; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739; D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1987, 109, 7151-7157.
37. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875; D. A. Evans, E. Vogel, J. V. Nelson, J. Am. Chem. Soc. 1979, 101, 6120-6123; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739; D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1987, 109, 7151-7157.
38. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875; D. A. Evans, E. Vogel, J. V. Nelson, J. Am. Chem. Soc. 1979, 101, 6120-6123; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739; D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1987, 109, 7151-7157.
39. D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835-875; D. A. Evans, E. Vogel, J. V. Nelson, J. Am. Chem. Soc. 1979, 101, 6120-6123; D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739; D. A. Evans, A. E. Weber, J. Am. Chem. Soc. 1987, 109, 7151-7157.