AZETIDIN-3-ONES FROM (S)-ALPHA-AMINO ACIDS AND THEIR REACTIONS WITH NUCLEOPHILES - PREPARATION OF SOME AZETIDINE-CONTAINING AMINO-ALCOHOL AND AMINO-ACID DERIVATIVES

被引：49

作者：

PODLECH, J ^{[1
]}

SEEBACH, D ^{[1
]}

机构：

[1] ETH ZENTRUM,ORGAN CHEM LAB,CH-8092 ZURICH,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1995年 / 78卷 / 05期

关键词：

D O I：

10.1002/hlca.19950780516

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reactions of azetidin-3-ones 6-10, readily available from the amino acids L-alanine, L-phenylalanine, L-valine. L-lysine, and L-aspartic acid, via the corresponding diazo ketones, with nucleophilic reagents such as complex hydrides, Grignard compounds, an ester enolate, and a Wittig ylide give the expected products 11-19 in good yields and mostly in high diastereoselectivities. New amino-alcohol, gamma-amino- and gamma-amino-beta-hydroxy-carboxplic-acid derivatives of known configurations are thus available.

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页码：1238 / 1246

页数：9

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