Highly π-facial stereoselective aldol reaction of (S)-proline-derived amide enolate with benzaldehydes

被引：3

作者：

Adam, W ^{[1
]}

Zhang, A ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 03期

关键词：

aldol reactions; stereoselectivity; reaction mechanism; X-ray diffraction;

D O I：

10.1002/ejoc.200390097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric aldol reaction of the (S)-proline-derived bicyclic amide enolate 1 with benzaldehydes selectively affords the two diastereomeric aldol adducts (3S,3'R,8S)-3a and (3S,3'S,8S)-3a, of four possible diastereomers, in good yield. The high control of pi-facial stereoselectivity at the en-docyclic C-3 stereocenter is due to perfect shielding by the pseudo-axial phenyl ring at the C-1 position.

引用

页码：587 / 591

页数：5

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