Asymmetric cyclopropanation of chiral (1-dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide:: a new synthesis of enantiomerically pure 2-amino-3-phenyl-1-cyclopropane-phosphonic acid -: a constrained analog of phaclofen

被引：35

作者：

Midura, WH ^{[1
]}

Mikolajczyk, M ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 16期

关键词：

asymmetric cyclopropanation; chiral alpha-phosphorylvinyl sulfoxides aminocyclopropanephosphonic acid;

D O I：

10.1016/S0040-4039(02)00374-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

E-(S)-(1-Dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 3 was found to undergo cyclopropanation with sulfur ylides [dimethyl(oxo)sulfonium methylide, diphenyl sulfonium isopropylide and ethyl (dimethylsulfuranylidene)acetate (EDSA)] in a highly diastereoselective manner. The major diastereomer obtained in the reaction of E-(S)-3 with EDSA vas converted into enantiopure (2R)-amino-(3R)-phenyl-(1R)-cyclopropane-phosphonic acid, a constrained analog of the GABA(B) antagonist. phaclofen. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：3061 / 3065

页数：5

共 29 条

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[2] ASYMMETRIC DIELS-ALDER REACTIONS OF CHIRAL (E)-2-CYANOCINNAMATES .2. SYNTHESIS OF THE 4 1-AMINO-2-PHENYL-1-CYCLOHEXANECARBOXYLIC ACIDS IN ENANTIOMERICALLY PURE FORM
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[10] Synthesis and antimicrobial activity of some hybrid 2-aryl-4-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)-2,3-dihydro-1H-benzo[b][1,4]diazepine derivatives
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