Asymmetric hetero Diels-Alder reaction of N-benzylimines derived from R-glyceraldehyde: A new approach to homochiral piperidine building blocks and its application to the synthesis of (2R)-4-oxopipecolic acid

被引:34
作者
Badorrey, R [1 ]
Cativiela, C [1 ]
DiazdeVillegas, MD [1 ]
Galvez, JA [1 ]
机构
[1] UNIV ZARAGOZA, CSIC, INST CIENCIA MAT ARAGON, DEPT QUIM ORGAN, E-50009 ZARAGOZA, SPAIN
关键词
D O I
10.1016/S0040-4039(97)00397-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The N-Benzyl imine derived from 23-di-O-benzyl-D-glyceraldehyde reacts with Danishefsky's diene to afford the corresponding hetero Diels-Alder adduct with a high diastereoselectivity. This compound can be transformed to enantiomerically pure (2R)-4-oxopipecolic acid. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2547 / 2550
页数:4
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