Facile enantiodivergence of meso-1,3-diacyl-2-imidazolidinones to chiral 2-imidazolidinone auxiliaries

Tetrahedron Letters

Volumn 39, Issue 27, 1998, Pages 4847-4850

  Yokoyama, Kazuhiro ^a   Ishizuka, Tadao ^a   Ohmachi, Naoko ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 IMIDAZOLIDINONE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; DEACETYLATION; ENANTIOMER; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032474699     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00918-6     Document Type: Article

References (16)

1. 1. For reviews, see : a) Evans, D.A. Aldrichimica Acta, 1982, 15, 23.
2. b) Ager, D.J. ; Prakash, I. ; Schaad, D.R. Chem. Rev. 1996, 96, 835.
3. c) idem, Aldrichimica Acta, 1997, 30, 3.
4. 2. For recent examples, see : a) Powers, T.S. ; Jiang, W. ; Su, J. ; Wulff, W.D. ; Waltermire, B.E. ; Rheingold, A.L. ; J. Am. Chem. Soc., 1997, 119, 6438.
5. b) van Heerden, P.S. ; Bezuidenhoudt, B.C.B. ; Ferreira, D. Tetrahedron Lett., 1997, 38, 1821.
6. 3. a) Matsunaga, H. ; Kimura, K. ; Ishizuka, T. ; Kunieda, T. Tetrahedron Lett., 1991, 32, 7715.
7. b) Kimura, K. ; Murata, K. ; Otsuka, K. ; Ishizuka, T. ; Haratake, M. ; Kunieda, T. Tetrahedron Lett., 1992, 33, 4461.
8. 4. Wang, P. C. Heterocycles, 1985, 23, 3041.
9. 5. The optical resolution was readily achieved via facile separation of (equation presented) the diastereomeric N-MAC derivatives, 16 and 17. For optical resolution of 2-oxazolidinones using (+)-MAC acid, see : Ishizuka, T. ; Kimura, K. ; Ishibuchi, S. ; Kunieda, T. Chem. Lett., 1992, 991.
10. 1) δ : 1.93 (6H, s), 2.39 (6H, s), 4.63 (2H, s). 7.23-7.43 (8H, m).
11. 7. Kimura, K. ; Sugiyama, E. ; Ishizuka, T. ; Kunieda, T. Tetrahedron Lett., 1992, 33, 3147.
12. 3,) δ : 1.92 (3H, s). 1.94 (3H, s), 2.41 (3H, s), 3.72 (1H, d. J=9.2Hz), 4.66 (1H, d, J=9.2Hz), 5.23 (1H, s), 7.20-7.42 (8H, m).
13. -1, R=0.039. The authors have deposited atomic coordinates for 7a and 7b with the Cambridge Crystallographic Data Center. They can be obtained, on request, from the Director of the Center.
14. 27+135.6° (c 1.00, MeOH).
15. 11. a) Evans, D.A. ; Chapman, K.T. ; Bisaha, J. J. Am. Chem. Soc., 1988, 110, 1238.
16. b) Kishikawa, K., Yamamoto, M., Kohmoto, S., Yamada, K. J. Org. Chem., 1989, 54, 2428.