Synthesis of β-cyclopropylalanines by photolysis of diacyl peroxides

被引：24

作者：

Jain, RP ^{[1
]}

Vederas, JC ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 24期

关键词：

D O I：

10.1021/ol035859a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis at 254 nm of neat (no solvent) unsymmetrical diacyl peroxides derived from cyclopropane carboxylic acids and L-aspartic acid generates protected beta-cyclopropylalanines in reasonable yields. Orthogonally protected 3-(trans-2-aminocyclopropyl)alanine (21), a key constituent of the antitumor agent belactosin A, as well as protected hypoglycin A (26), a causative agent of Jamaican vomiting sickness, is synthesized by this approach with coupling. of the intermediate substituted cyclopropyl radicals proceeding predominantly with retention of configuration (dr greater than or equal to 95:5).

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页码：4669 / 4672

页数：4

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