DERACEMIZATION OF AXIALLY DISSYMMETRIC COMPOUNDS BY ENANTIOSELECTIVE DEHYDROHALOGENATION USING CHIRAL LITHIUM AMIDES .2.

被引:16
作者
DUHAMEL, L
RAVARD, A
PLAQUEVENT, JC
机构
[1] URA D 0464, UFR Sciences et Techniques, Université de Rouen, F 76134 Mont Saint Aignan Cedex
关键词
D O I
10.1016/0957-4166(90)90030-E
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
New findings about deracemization of unsaturated carboxylic acids 1 by enantioselective dehydrohalogenation of prochiral species 2 by chiral lithium amides leading to axially dissymmetric compounds with 80% e.e. are reported. The role of the structure of the prochiral hydrochlorinated intermediate is discussed. An example of axial to central chirality transfer is described. (1a → 3). © 1990.
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页码:347 / 350
页数:4
相关论文
共 17 条
[1]   ENANTIOSELECTIVE DEHYDROHALOGENATION VIA ASYMMETRIC DEPROTONATION BY CHIRAL LITHIUM AMIDES - DERACEMIZATION OF A COMPOUND BEARING A CHIRAL AXIS [J].
DUHAMEL, L ;
RAVARD, A ;
PLAQUEVENT, JC ;
DAVOUST, D .
TETRAHEDRON LETTERS, 1987, 28 (45) :5517-5520
[2]   DERACEMIZATION BY ENANTIOSELECTIVE PROTONATION .4. AN IMPROVED METHOD FOR THE ENANTIOMERIC ENRICHMENT OF ALPHA-AMINOACIDS USING METALATION BY MEANS OF CHIRAL AMIDES [J].
DUHAMEL, L ;
PLAQUEVENT, JC .
TETRAHEDRON LETTERS, 1980, 21 (26) :2521-2524
[3]   ENANTIOSELECTIVE ELECTROPHILIC BOND CONSTRUCTION TO THE ALPHA-CARBON OF ALPHA-AMINOACIDS [J].
DUHAMEL, L ;
DUHAMEL, P ;
FOUQUAY, S ;
EDDINE, J ;
PESCHARD, O ;
PLAQUEVENT, JC ;
RAVARD, A ;
SOLLIARD, R ;
VALNOT, JY ;
VINCENS, H .
TETRAHEDRON, 1988, 44 (17) :5495-5506
[4]  
DUHAMEL L, 1982, B SOC CHIM FR, pR2
[5]   SYNTHESES OF CHIRAL CYCLOHEXYLIDENEPROPENES AND CYCLOHEXYLIDENEACETALDEHYDES [J].
DURAISAMY, M ;
WALBORSKY, HM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3252-3264
[6]   UBER DIE CHIRALITAT DER ENANTIOMEREN 4-METHYLCYCLOHEXYLIDENESSIGSAUREN [J].
GERLACH, H .
HELVETICA CHIMICA ACTA, 1966, 49 (04) :1291-&
[7]   THE REGIOSELECTIVE DEPROTONATION OF CONJUGATED ACIDS [J].
HARRIS, FL ;
WEILER, L .
TETRAHEDRON LETTERS, 1985, 26 (16) :1939-1942
[8]  
HARRIS FL, 1984, TETRAHEDRON LETT, V25, P1333
[9]  
NUNAMI KI, 1978, J CHEM SOC P1, P2224
[10]  
PERKIN WH, 1911, J CHEM SOC, P1510