DIRECT DERIVATIZATION OF GLYOXAL INTO CHIRAL TEMPLATES PROVIDING COMPLETE DISCRIMINATION BETWEEN THE ALDEHYDE GROUPS

被引：29

作者：

AGAMI, C

COUTY, F

HAMON, L

PRINCE, B

PUCHOT, C

机构：

[1] Laboratoire de Chimie Organique (URA CNRS 408) Université P. et M. Curie, 75005 Paris

来源：

TETRAHEDRON | 1990年 / 46卷 / 20期

关键词：

D O I：

10.1016/S0040-4020(01)87885-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation between glyoxal thiophenol and N-substituted (R)-phenylglycinol led to morpholine derivatives. The totally stereoselective formation of heterocycle 6 gives access to a chiral masked form of glyoxal in which the symmetry features of the dialdehyde have disappeared. The cyclisation is consistent with Baldwin rules for ring closures when applied to different competing pathways. AMI conformational calculations were used in order to rationalize the stereochemical outcome of the reported transformation. © 1990.

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页码：7003 / 7010

页数：8

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