Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected β-aminoaldehydes and benzyl diazoacetate

被引：17

作者：

Angle, SR ^{[1
]}

Belanger, DS ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 13期

关键词：

D O I：

10.1021/jo030360f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a series of 3-hydroxyproline benzyl esters from alpha-alkyl and alpha-alkoxy N-protected aminoaldehydes with benzyl diazoacetate is described. Aldehydes with alpha-alkyl substituents afforded prolines as a single diastereomer with a trans-cis relative configuration in 14-77%. An alpha-tert-butyldimethylsilyloxy aminoaldehyde afforded a proline as a single diastereomer with a trans-trans relative configuration in 37% yield.

引用

页码：4361 / 4368

页数：8

共 45 条

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