Efficient diastereo- and enantioselective synthesis of α,β-disubstituted γ-phosphono sulfonates

被引：9
|
作者：
Enders, Dieter [1 ]
Mirjafary, Zohreh [1 ,2 ]
Saeidian, Hamdollah [1 ,2 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Sharif Univ Technol, Dept Chem, Tehran, Iran
来源：
TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 21期
关键词：
ORGANOCATALYTIC CONJUGATE ADDITION; ASYMMETRIC-SYNTHESIS; NATURAL-PRODUCTS; MICHAEL ADDITION; DERIVATIVES; INHIBITORS; ALDEHYDES; NITRO; ACIDS;
D O I：
10.1016/j.tetasy.2009.10.011
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The first asymmetric synthesis of alpha,beta-disubstituted gamma-phosphono sulfonates is reported. The key step is the Michael addition of a lithiated enantiopure sulfonate bearing an inexpensive chiral sugar auxiliary to alpha,beta-unsaturated phosphonates in good diastereoselectivities. After chromatographic purification, the cleavage of the chiral sugar auxiliary proceeds without any epimerization or racemization to form the corresponding isopropyl sulfonate in very good overall yield (75%) and excellent diastereomeric and enantiomeric excess (de, ee >= 95%). (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2429 / 2431
页数：3
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