SYNTHESIS OF CHIRAL SULFAHYDANTOINS - STEREOCHEMICAL ASPECTS AND REGIOSPECIFIC PROTECTION

被引：27

作者：

DEWYNTER, G

AOUF, N

CRITON, M

MONTERO, JL

机构：

[1] UNIV MONTPELLIER SCI & TECH LANGUEDOC 2,CHIM BIOORGAN LAB,CNRS,UA 488,PL E BATAILLON,F-34095 MONTPELLIER 5,FRANCE

[2] UNIV ANNABA,INST CHIM,CHIM ORGAN LAB,EL HADJAR,ALGERIA

来源：

TETRAHEDRON | 1993年 / 49卷 / 01期

关键词：

CHLOROSULFONYL ISOCYANATE; CARBOXYLSULFAMIDES; MITSUNOBU REACTION; SULFAHYDANTOINS;

D O I：

10.1016/S0040-4020(01)80506-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiospecific synthesis of N2-benzyl-1-thia-2,5-diazolidin-3-one dioxides (sulfa-analogues of hydantoins) was carried out through two convergent pathways starting from chlorosulfonyl isocyanate (CSI) and chiral alpha amino- and hydroxyesters. The intermediate carboxylsulfamides (containing ''activated sulfamoyl group'') react easily in the Mitsunobu conditions to give ultimately the N-protected sulfa-hydantoins, or symmetric and dissymmetric sulfones of bis-N-aminoesters. The non-racemization during the cyclization of N-sulfamylaminoesters in alkaline conditions was established by chemical and spectroscopic methods (nmr with chiral Eu(hfc)3).

引用

页码：65 / 76

页数：12

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