Chiral aminals: Powerful auxiliaries in asymmetric synthesis

被引：57

作者：

Alexakis, A

Mangeney, P

Lensen, N

Tranchier, JP

Gosmini, R

Raussou, S

机构：

[1] Laboratoire de Chimie des Organo-Eléments, associé au CNRS UA 473, Université P. et M. Curie, F-75252 Paris Cedex 05, 4, Place Jussieu

来源：

PURE AND APPLIED CHEMISTRY | 1996年 / 68卷 / 03期

关键词：

D O I：

10.1351/pac199668030531

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral aminals are prepared from chiral C2 symmetrical diamines and aldehydes. The chiral imidazolidine ring exerts its stereocontrol either through steric or chelation effects. Reaction of aqueous glyoxal with diamine 1 results in a new chiral synthon 6; this ''chiron'' is a useful precursor for alpha-hydroxy aldehydes and for alpha-amino aldehydes. An aminal of nicotinaldehyde 7 reacts stereoselectively with organocopper reagents to afford a chiral dihydropyridine, which is a starting point for several shea asymmetric syntheses of indolo- and benzo-quinolizine alkaloids.

引用

页码：531 / 534

页数：4

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