Highly stereospecific S(N)2-type displacement of sulfinyl by hydroxy group under Pummerer conditions

被引：27

作者：

Bravo, P ^{[1
]}

Zanda, M ^{[1
]}

Zappala, C ^{[1
]}

机构：

[1] POLITECN MILAN,DIPARTIMENTO CHIM,CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20131 MILAN,ITALY

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 33期

关键词：

D O I：

10.1016/0040-4039(96)01260-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trifluoroacetic anhydride promoted Pummerer reactions of N-Cbz alpha-amino-alpha-trifluoromethyl-beta-p-tolylsulfinyl methyl butanoates 1b-c occur in a highly stereospecific non-oxidative fashion (d.r. > 98:2), resulting in a S(N)2-lype displacement of the sulfinyl by hydroxy group and providing enantiomerically pure alpha-trifluoromethyl-allo-threonine 2b and -threonine 2c derivatives. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：6005 / 6006

页数：2

共 13 条

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[J]. TETRAHEDRON, 1996, 52 (01) : 279 - 290

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