SYNTHETICALLY USEFUL C-4 FLUORINATED BUILDING-BLOCKS BEARING A QUATERNARY STEREOCENTER

被引：14
作者：
ARNONE, A
BRAVO, P
FRIGERIO, M
SALANI, G
VIANI, F
机构：
[1] C.N.R. - Centro, Studio sulle Sostanze Organiche Naturali - Dipartimento di Chimica, Politecnico di Milano -, I- 20131 Milano
来源：
TETRAHEDRON | 1994年 / 50卷 / 47期
关键词：
D O I：
10.1016/S0040-4020(01)89355-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
the syntheses of 2-fluoromethyl-2-hydroxymehtyl-, 2-(dimethoxy)methyl-2-fluoromethyl- and 2-carboxy-2-fluoromethyl oxiranes 5, 7, and 8 through reaction of diazomethane with beta-keto-gamma-fluorosubstituted sulphoxide 1 followed by Pummerer rearrangement are shown. Selected oxirane opening reactions with nitrogen nucleophiles to give beta, gamma-dihydroxy-beta-fluoromethyl amine 14 and alpha-hydroxy-alpha-fluoromethyl-beta-amino acid 19 are described.
引用
收藏
页码：13485 / 13492
页数：8
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