CHIRAL AMINAL TEMPLATES .3. DIASTEREOSELECTIVITY OF ORGANOMETALLIC ATTACK ON ALDEHYDES BEARING A CHIRAL IMIDAZOLIDINE GROUP

被引：29

作者：

ALEXAKIS, A

SEDRANI, R

NORMANT, JF

MANGENEY, P

机构：

[1] Laboratoire de Chimie des Organoéléments, CNRS URA 856 Université P. et M. Curie, F-75252 Paris Cedex 05

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 05期

关键词：

D O I：

10.1016/S0957-4166(00)86314-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Monoprotected phthalaldehydes 3 and 4, bearing a chiral imidazolidine auxiliary were reacted with various organometallic reagents. Lithium organocuprates gave almost exclusively one diastereomer whereas an organomanganese reagent gave the opposite one. Hydrolysis of the aminal moiety affords the enantiomerically pure lactols 7a-d. In both 3 and 4 the chiral imidazolidine auxiliary is very effective, but affords opposite results which are rationalized by chelation and/or steric factors. © 1990.

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页码：283 / 286

页数：4

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