Asymmetric ring opening reactions of symmetrical N-acylaziridines with thiols catalyzed by chiral dialkyl tartrate-diethylzinc complexes

Tetrahedron

Volumn 52, Issue 23, 1996, Pages 7817-7832

  Hayashi, Masahiko ^a   Ono, Kazuyuki ^a   Hoshimi, Haruhisa ^a   Oguni, Nobuki ^a  

^a YAMAGUCHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ENANTIOMER; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; PRIORITY JOURNAL; SYNTHESIS;

EID: 0030029806     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00370-5     Document Type: Article

References (25)

1. (a) Irwin, A. J.; Jones, J. B. J. Am. Chem. Soc. 1977, 99, 556. Jakovac, I. J.; Ng, C.; Lok, K. P.;. Jones, J. B.J. Chem. Soc., Chem. Commun. 1980, 515. Jakivac, I. J.; Goodbrand, H. B.; Lok, K. P. Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659;
2. (a) Irwin, A. J.; Jones, J. B. J. Am. Chem. Soc. 1977, 99, 556. Jakovac, I. J.; Ng, C.; Lok, K. P.;. Jones, J. B.J. Chem. Soc., Chem. Commun. 1980, 515. Jakivac, I. J.; Goodbrand, H. B.; Lok, K. P. Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659;
3. (a) Irwin, A. J.; Jones, J. B. J. Am. Chem. Soc. 1977, 99, 556. Jakovac, I. J.; Ng, C.; Lok, K. P.;. Jones, J. B.J. Chem. Soc., Chem. Commun. 1980, 515. Jakivac, I. J.; Goodbrand, H. B.; Lok, K. P. Jones, J. B. J. Am. Chem. Soc. 1982, 104, 4659;
4. (b) Ohno, M.; Kobayashi, S.; Iimori, T.; Wang, Y.-F.; Izawa, T. J. Am. Chem. Soc. 1981, 103, 2405. Kobayashi, S.; Iimori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406.
5. (b) Ohno, M.; Kobayashi, S.; Iimori, T.; Wang, Y.-F.; Izawa, T. J. Am. Chem. Soc. 1981, 103, 2405. Kobayashi, S.; Iimori, T.; Izawa, T.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 2406.
6. (a) Nagao, Y.; Ikeda, T.; Yagi, M.; Fujita, E.; Shiro, M. J. Am. Chem. Soc. 1982, 104, 2079;
7. (b) Osakada, K.; Obana, M.; Ikariya, T.; Saburi, M.; Yoshikawa, S. Tetrahedron Lett. 1981, 22, 4297;
8. (c) Fujisawa, T.; Watanabe, M.; Sato, T. Chem. Lett. 1984, 2055;
9. (d) Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1980, 45, 755;
10. (e) Asami, M. Chem. Lett. 1984, 829;
11. (f) Davies, S. G.; Warner, P. Tetrahedron Lett. 1985, 26, 4815;
12. (g) Asami, M. Tetrahedron Lett. 1985, 26, 5803.
13. Yamashita, H.; Mukaiyama, T. Chem. Lett. 1985, 1643.
14. (a) Yamashita, H. Chem. Lett. 1987, 525.
15. (b) Joshi, N. N.; Srebnik, M.; Brown, H. C. J. Am. Chem. Soc. 1988, 110, 6246;
16. (c) Emziane, M.; Sutowardoyo, K. I.; Sinou, D. J. J. Organomet. Chem. 1988, 346, C7;
17. (d) Tomoda, S.; Iwaoka, M. J. Chem. Soc., Chem. Commun. 1988, 1283;
18. (e) Hayashi, M.; Kohmura, K.; Oguni, N. Synlett 1991, 774;
19. (f) Chan, A. S. C.; Coleman, J. P. J. Chem. Soc., Chem. Commun. 1991, 535;
20. (g) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768;
21. (h) Martínez, L. E.; Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5897
22. Recently Scheffold reported the isomerization of achiral N-acylaziridines to optically active N-acyl-allylic amines catalyzed by cob(I)alamin: Zhang, Z.; Scheffold, R. Helv. Chim. Acta 1993, 76, 2602.
23. For preliminary results, see: Hayashi, M.; Ono, K.; Hoshimi, H.; Oguni, N. J. Chem. Soc., Chem. Commun. 1994, 2699.
24. 3.
25. Winternitz, F.; Mousseron, M.; Dennilauler, R. Bull. Soc. Chim. Fr. 1956, 382.