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
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
收藏
页码:1074 / 1076
页数:3
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