Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

被引：16
作者：
Pesenti, C
Arnone, A
Arosio, P
Frigerio, M
Meille, SV
Panzeri, W
Viani, F
Zanda, M
机构：
[1] CNR, Ist Chim Riconoscimento Mol, Sez A Quilico, I-20131 Milan, Italy
[2] Mat Ingn Chim G Natta Politecn Milano, Dipartimento Chim, I-20131 Milan, Italy
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 26期
关键词：
peptidomimetics; sulfoxides; Mannich reaction;
D O I：
10.1016/j.tetlet.2004.04.160
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel synthesis of enantiopure hydroxyethylamine isosteres has been developed. Reaction of lithiated beta-sulfinyl-ethylamines 3 with N-Cbz-irnines generated in situ from alpha-amino-sulfones 4 afforded in good to excellent yields and moderate stereocontrol the 2-sulfinyl-1,3-diamines 2. The latter were submitted to the nonoxidative Pummerer reaction (NOPR) in CH2Cl2, that produced the target compounds 1 in very good yields with inversion Of Configuration. In some cases, the use of acetonitrile as solvent resulted in a double-inversion pathway, leading for example to the oxazolidinone 5. The total synthesis of an epimer of Saquinavir has been achieved by this method. (C) 2004 Elsevier Ltd. All rights reserved.
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收藏
页码：5125 / 5129
页数：5
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