Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition

被引：43

作者：

Arena, Giada ^{[1
]}

Chen, C. Chun ^{[1
]}

Leonori, Daniele ^{[1
]}

Aggarwal, Varinder K. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 16期

基金：

欧洲研究理事会; 英国工程与自然科学研究理事会;

关键词：

CHIRAL NITRIDOMANGANESE COMPLEX; HIGHLY SUBSTITUTED PYRROLIDINES; CATALYZED CASCADE REACTIONS; EXCITATORY AMINO-ACIDS; ENE-TYPE REACTIONS; ACTIVATED OLEFINS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; KAINIC ACID; (+/-)-ALPHA-ALLOKAINIC ACID;

D O I：

10.1021/ol4020333

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Methyl vinyl aziridine undergoes a mild MgI2-promoted S(N)2' ring opening and concomitant cyclization with fumarate Michael acceptors to give trisubstituted pyrrolidines. The process is efficient and highly diastereoselective. This methodology has been applied to a concise asymmetric synthesis of (+)-allo-kainic acid.

引用

页码：4250 / 4253

页数：4

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