Enantiopure Trans-4,5-Disubstituted 2-Imidazolidinones via Copper(I)-Catalyzed Ring Opening of 1,1′-DiBoc-2,2′-Biaziridine with Grignard Reagents

被引：7

作者：

Kennedy, Matthew D. ^{[1
]}

Bailey, Stephen J. ^{[1
]}

Wales, Steven M. ^{[1
]}

Keller, Paul A. ^{[1
]}

机构：

[1] Univ Wollongong, Sch Chem, Wollongong, NSW 2522, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

关键词：

MAGNESIUM EXCHANGE-REACTION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC DIAMINATION; CONJUGATED DIENES; ACID-DERIVATIVES; VICINAL DIAMINES; TERMINAL OLEFINS; CARBOXYLIC-ACIDS; CYCLIC UREAS; AMINO-ACIDS;

D O I：

10.1021/acs.joc.5b00832

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper-catalyzed ring opening of chiral-pool-derived 1,1'-diBoc-2,2'-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C-C bond constructions concurrent to imidatolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.

引用

页码：5992 / 5998

页数：7

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