Diastereoselective synthesis of cyclopropane amino acids using diazo compounds generated in situ

被引：92

作者：

Adams, LA ^{[1
]}

Aggarwal, VK ^{[1
]}

Bonnert, RV ^{[1
]}

Bressel, B ^{[1
]}

Cox, RJ ^{[1
]}

Shepherd, J ^{[1
]}

de Vicente, J ^{[1
]}

Walter, M ^{[1
]}

Whittingham, WG ^{[1
]}

Winn, CL ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 24期

关键词：

D O I：

10.1021/jo035060c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1,3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (+/-)-(Z)-2,3-methanophenylalanine [(+/-)-(Z)-1], the anti-Parkinson (+/-)-(E)-2,3-methano-m-tyrosine [(+/-)-(E)-2], and the natural product (+/-)-coronamic acid [(+/-)-3].

引用

页码：9433 / 9440

页数：8

共 52 条

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