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
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
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页码:6005 / 6006
页数:2
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