Chloroperoxidase-mediated asymmetric epoxidation. Synthesis of (R)-dimethyl-2-methylaziridine-1,2-dicarboxylate - a potential alpha-methylamino acid synthon

被引:34
作者
Lakner, FJ [1 ]
Hager, LP [1 ]
机构
[1] UNIV ILLINOIS,DEPT BIOCHEM,URBANA,IL 61801
关键词
D O I
10.1016/S0957-4166(97)00467-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Methoxycarbonyl-protected methallyl amine serves as an excellent substrate for chloroperoxidase-mediated asymmetric epoxidation. The resulting (R)-epoxide (94% ee) was converted to the title compound in three steps with nearly complete maintenance of stereochemical integrity. Titanium tetrachloride ring-opening of the epoxide provided the chlorohydrin with excellent selectivity and inversion of the stereogenic center. Oxidation with pyridinium dichromate was followed by ring-closure to the aziridine which was esterified in situ with methyl iodide. (C) 1997 Elsevier Science Ltd.
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页码:3547 / 3550
页数:4
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