Copper-catalyzed desymmetrization of N-sulfonylaziridines with methylmagnesium halides

被引：70

作者：

Muller, P ^{[1
]}

Nury, P ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 03期

关键词：

D O I：

10.1021/ol990650b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclohexene N-p-toluenesulfonylimine (1) undergoes enantioselective ring opening to 2b upon treatment with methylmagnesium halides or MeLi in the presence of chiral Cu catalysts. No activation of the aziridine by Lewis acid is required. Enantioselectivities of up to 91% have been observed under optimized conditions with the chiral imine ligand derived from phenylalanine. The same system reacts with cyclohexene oxide to afford trans-2-methylcyclohexanol with 50% yield and 10% ee.

引用

页码：439 / 441

页数：3

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