ASYMMETRIC ALDOL AND ALKYLATION REACTIONS MEDIATED BY THE QUAT CHIRAL AUXILIARY (R)-(-)-5-METHYL-3,3-DIMETHYL-2-PYRROLIDINONE

被引:33
作者
DAVIES, SG
DOISNEAU, GJM
PRODGER, JC
SANGANEE, HJ
机构
[1] The Dyson Perrins Laboratory, University of Oxford, Oxford, OX1 3QY, South Parks Road
关键词
D O I
10.1016/0040-4039(94)85223-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enolates derived from the N-propionoyl derivative of the ''quat'' chiral auxiliary (R)-(-)-5-methyl-3,3-dimethyl-2-pyrrolidinon undergo highly stereoselective aldol and alkylation reactions. Removal of the auxiliary has been demonstrated with LiOH, PhCH(2)OLi, MeOMgBr and LiA1H(4) to generate respectively (2R,3R)-3-hydroxy-2-methyl-3-phenylpropionic acid in homochiral form, and with 96% e.e. (S)-2-methyl-3-phenylpropionic acid and derived methyl and benzyl esters and with >94% e.e. (S)-2-methyl-3-phenylpropanol.
引用
收藏
页码:2373 / 2376
页数:4
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