N-PHTHALIMIDOAZIRIDINES BY DIASTEREOSELECTIVE ADDITION TO ALPHA,BETA-UNSATURATED AMIDES - A ROUTE TO CHIRAL BETA-SUBSTITUTED ALPHA-HYDRAZINO ACID-DERIVATIVES

被引：29

作者：

KAPRON, JT ^{[1
]}

SANTARSIERO, BD ^{[1
]}

VEDERAS, JC ^{[1
]}

机构：

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

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 13期

关键词：

D O I：

10.1039/c39930001074

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lead tetraacetate oxidation of N-aminophthalimide 1 in the presence of N-enoylbornane[10,2]sultams (Oppolzer auxiliary) generates corresponding N-phthalimidoaziridine adducts (12-94% yield) with 33% to greater-than-or-equal-to 95% diastereofacial selectivity (syn attack at the re face of the alpha-carbon for 4a); these chiral N-aminoaziridine derivatives readily undergo ring opening by sulfur nucleophiles to give alpha-hydrazino acid derivatives.

引用

页码：1074 / 1076

页数：3

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