Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: Asymmetric synthesis of cispentacin

被引：60

作者：

Aggarwal, VK

Roseblade, SJ

Barrell, JK

Alexander, R

机构：

[1] Univ Bristol, Dept Chem, Slough SL1 4EN, Berks, England

[2] Celltech R&D Ltd, Slough SL1 4EN, Berks, England

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 07期

关键词：

D O I：

10.1021/ol025665f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly diastereoselective intramolecular nitrone cycloaddition onto a chiral ketene equivalent, obtained by Horner-Wadsworth-Emmons olefination of either enantiomer of bis-sulfinyl phosphonate 6, is described. Cycloaddition gave 5,5-disubstituted isoxazolidine 10 in good yield as a single diastereomer. Catalytic hydrogenolysis of 10 furnished either enantiomer of optically pure cis-2-aminocyclopentane-1-carboxylic acid.

引用

页码：1227 / 1229

页数：3

共 42 条

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