HIGHLY ENANTIOSELECTIVE SYNTHESIS OF PIPECOLIC ACID-DERIVATIVES VIA AN ASYMMETRIC AZA-DIELS-ALDER REACTION

被引：51

作者：

BAILEY, PD

LONDESBROUGH, DJ

HANCOX, TC

HEFFERNAN, JD

HOLMES, AB

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

[2] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 22期

关键词：

D O I：

10.1039/c39940002543

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Very high asymmetric induction is observed in the aza-Diels-Alder reaction between dienes and the imine (R)-PhMeCH-N=CHCO(2)PhMen* (where PhMen* = 8-phenylmenthyl), which bears matched auxiliaries on nitrogen and on the ester; reactions in trifluoroethanol, in the presence of trifluoroacetic acid (1 equiv.), give substituted pipecolic acid derivatives in ca 50% isolated yield, with only a single regio- and diastereo-isomer of the-cycloadduct detectable in all cases (d.e. >95%).

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页码：2543 / 2544

页数：2

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