The first synthesis of enantiomerically pure cyclopropylphosphonate analogues of nucleotides via asymmetric cyclopropanation of chiral (1-diethoxyphosphoryl)vinyl p-tolyl sulfoxide

被引：28

作者：

Midura, WH ^{[1
]}

Krysiak, JA ^{[1
]}

Mikolajczyk, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(03)00211-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(S)-(+)-(1-Diethoxyphosphoryl)vinyl p-tolyl sulfoxide undergoes cyclopropanation with ethyl (dimethylsulfuranylidene)acetate (EDSA) in a highly diastereoselective manner (facial stereoselectivity up to 12:1). The major diastereomer obtained in this reaction, (1S,2S)-(1-diethoxyphosphoryl-2-ethoxycarbonyl)cyclopropyl p-tolyl sulfoxide, was converted in three steps into enantiopure cyclopropylphosphonate analogues of purine nucleotides as the constrained forms of antiviral 1-alkenylphosphonic acid derivatives of purines. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1245 / 1249

页数：5

共 18 条

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CHEMICAL COMMUNICATIONS, 1998, (10) : 1109 - 1110
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TETRAHEDRON LETTERS, 2002, 43 (16) : 3061 - 3065
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TETRAHEDRON, 1999, 55 (10) : 3025 - 3040
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