ASYMMETRIC ADDITION OF METHYL NITROACETATE TO CROTONALDEHYDE CATALYZED BY CHIRAL AMINES

被引:16
作者
BELOKON, YN
KOCHETKOV, KA
CHURKINA, TD
IKONNIKOV, NS
ORLOVA, SA
KUZMINA, NA
BODROV, DE
机构
[1] A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, 117813
关键词
ASYMMETRIC MICHAEL ADDITION; CHIRAL AMINES; CATALYSIS; METHYL NITROACETATE; CROTONALDEHYDE; (S)-PROLINOL; 3-METHYLPROLINE; ENANTIOMERIC EXCESS;
D O I
10.1007/BF00699188
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The asymmetric Michael addition of methyl nitroacetate to crotonaldehyde catalyzed by chiral amines was carried out. The maximum chemical yield of diastereomeric products amounted to 95 %. The best asymmetric induction (42 % e.e.) was achieved in the case of catalysis by (S)-prolinol. The diastereomeric mixture was converted to a mixture of stereoisomeric 3-methyl-2-methoxycarbonylpyrrolidines. Absolute configurations of (2S,3S)- and (2R,3S)-isomers formed in excess were determined using GLC by comparison with authentic samples of racemic and optically pure forms of 3-methylproline.
引用
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页码:1525 / 1529
页数:5
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