ENANTIOSELECTIVE MICHAEL-TYPE REACTION OF CHIRAL LINEAR ALPHA,ALPHA-DISUBSTITUTED SECONDARY ENAMINES

被引：14

作者：

FELK, A

REVIAL, G

VIOSSAT, B

LEMOINE, P

PFAU, M

机构：

[1] ECOLE SUPER PHYS & CHIM IND VILLE PARIS,CNRS,UA 476,CHIM ORGAN LAB,F-75231 PARIS 05,FRANCE

[2] UNIV PARIS 05,PHYS LAB,F-75270 PARIS 06,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80112-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective Michael-type reaction of chiral 2-substituted cyclic imines, reacting as their secondary enamine tautomers, has been extended to a linear ketimine possessing an oxo group on one of the substituents. A single secondary enamine tautomer is observed due to H-bonding of the NH group, thus allowing the reaction to proceed with a high degree of stereoselectivity.

引用

页码：1459 / 1462

页数：4

共 9 条

[1] THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES
DANGELO, J
DESMAELE, D
DUMAS, F
GUINGANT, A
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (04) : 459 - 505
[2] PFAU M, 1979, B SOC CHIM FR II-CH, P627
[3] ENANTIOSELECTIVE SYNTHESIS OF QUATERNARY CARBON CENTERS THROUGH MICHAEL-TYPE ALKYLATION OF CHIRAL IMINES
PFAU, M
REVIAL, G
GUINGANT, A
DANGELO, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (01) : 273 - 274
[4] REVIAL G, UNPUB
[5] REVIAL G, 1991, ORG SYNTH, V70, P35
[6] A THEORETICAL INVESTIGATION OF ENANTIOSELECTIVITY - MICHAEL REACTION OF SECONDARY ENAMINES WITH ENONES
SEVIN, A
MASURE, D
GIESSNERPRETTRE, C
PFAU, M
[J]. HELVETICA CHIMICA ACTA, 1990, 73 (03) : 552 - 573
[7] TOWARD A TRANSITION-STATE MODEL IN THE ASYMMETRIC ALKYLATION OF CHIRAL KETONE SECONDARY ENAMINES BY ELECTRON-DEFICIENT ALKENES - A THEORETICAL MO STUDY
SEVIN, A
TORTAJADA, J
PFAU, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (14) : 2671 - 2675
[8] Sheldrick G.M, 1986, SHELXS86 PROGRAM CRY
[9] SHELDRICK GM, 1976, SHELX PROGRAM CRYSTA

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