Enantioselective Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagents to Imines

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 109-110

  Itsuno, Shinichi ^a   Watanabe, Katsuhiro ^a   Ito, Koichi ^a   El Shehawy, Ashraf A ^a   Sarhan, Ali A ^b  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b Mansoura University   (Egypt)

Author keywords

Amines; Asymmetric allylations; Boron; Imines

Indexed keywords

EID: 0030837580     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701091     Document Type: Article

References (25)

1. For a review on reaction of allylmetals with imines, see: E. F. Kleinman, R. A. Volkmann in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 975.
2. a) Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. Soc. 1986, 108, 7778;
3. b) T. Basile, A. Bocoum, D. Savoia, A. Umani-Ronchi, J. Org. Chem. 1994, 59, 7766;
4. c) D. Enders, J. Schankat, M. Klatt, Synlett 1994, 795;
5. d) Y. Hashimoto, K. Takaoki, A. Sudo, T. Ogasawara, K. Saigo, Chem. Lett. 1995, 235.
6. For recent reviews on selective reactions using allylmetals, see: a) Y. Yamamoto, Acc. Chem. Res. 1987, 20, 243; b) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
7. For recent reviews on selective reactions using allylmetals, see: a) Y. Yamamoto, Acc. Chem. Res. 1987, 20, 243; b) Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207.
8. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
9. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
10. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
11. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
12. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
13. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
14. Asymmetric alkylation of imines: a) S. Itsuno, M. Sasaki, S. Kuroda, K. Ito, Tetrahedron: Asymmetry 1995, 6, 1507-1510; b) S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341; c) S. Itsuno, C. Hachisuka, K. Kitano, K. Ito, Tetrahedron Lett. 1992, 33, 627-630. Asymmetric reduction of imines: d) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans. 1 1990, 1859-1863; e) S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, ibid. 1989, 1548; f) S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, ibid. 1985, 2039; g) S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, S. Nakahama, Polymer 1987, 28, 1005.
15. D. J. Hart, D.-C. Ha, Chem. Rev. 1989, 89, 1447.
16. Allylborane 1 was developed by Brown et al. and used for enantioselective allylboration of aldehydes. See: a) H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092; b) U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401.
17. Allylborane 1 was developed by Brown et al. and used for enantioselective allylboration of aldehydes. See: a) H. C. Brown, P. K. Jadhav, J. Am. Chem. Soc. 1983, 105, 2092; b) U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401.
18. P. G. M. Wuts, Y.-W. Jung, Tetrahedron Lett. 1986, 27, 2079.
19. Y. Yamamoto, W. Ito, Tetrahedron 1988, 44, 5415.
20. N-Trimethylsilylimines were prepared according to the method of Hart, which is limited to nonenolizable carbonyl compounds. See: D. J. Hart, K. Kanai, D. G. Thomas, T.-K. Yang, J. Org. Chem. 1983, 48, 289.
21. The methanesulfonyl derivative of 8 was used as the chiral ligand in an allylating agent that was employed to asymmetric allylation of aldehydes. See: M. T. Reetz, T. Zierke, Chem. Ind. 1988, 663.
22. S. Schröder, K.-H. Thiele, Z. Anorg. Allg. Chem. 1977, 428, 225.
23. a) W. Oppolzer, C. Chapuis, Tetrahedron Lett. 1984, 25, 5383;
24. b) K. Tanaka, H. Ushio, H. Suzuki, J. Chem. Soc. Chem. Commun. 1989, 1700.
25. This compound is already known, and its spectroscopic data are in good agreement with those described in the literature [2b].