Synthesis of a chiral azodicarboxamide containing abridging binaphthyl moiety: Electrophilic amination reactions of achiral ester enolates

被引：27

作者：

Harris, JM ^{[1
]}

McDonald, R ^{[1
]}

Vederas, JC ^{[1
]}

机构：

[1] UNIV ALBERTA,DEPT CHEM,EDMONTON,AB T6G 2G2,CANADA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 22期

关键词：

D O I：

10.1039/p19960002669

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral azodicarboxamide 11 containing a bridging binaphthyl group has-been prepared by an intermolecular cyclization reaction between the bis(N-methylamine) of 2,2'-dimethyl-1,1'-binaphthyl 6 and N,N'-bis(azidocarbonyl)hydrazine 9, followed by oxidation of the resulting hydrazodicarboxamide 10 with N-bromosuccinimide and pyridine. The crystal structure of azodicarboxamide 11 has been determined, Reaction of 11 with achiral oxazolidinone anions at -78 degrees C gives alpha-hydrazino acid derivatives with high stereoselectivity. The stereochemical outcome of the amination was determined by X-ray crystallography.

引用

页码：2669 / 2674

页数：6

共 34 条

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