ASYMMETRIC-SYNTHESIS OF TRISUBSTITUTED GEM-DIFLUOROCYCLOHEXANES BY INTRAMOLECULAR TRAPPING OF DIFLUOROALKYL RADICALS

被引：8

作者：

ARNONE, A ^{[1
]}

BRAVO, P ^{[1
]}

VIANI, F ^{[1
]}

CAVICCHIO, G ^{[1
]}

机构：

[1] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67100 LAQUILA,ITALY

来源：

TETRAHEDRON-ASYMMETRY | 1991年 / 2卷 / 06期

关键词：

ASYMMETRIC SYNTHESIS; DIFLUOROCYCLOHEXANES; DIFLUOROALKYL RADICALS;

D O I：

10.1016/S0957-4166(00)82161-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

gem-Difluorocyclohexanols 8 bearing a methyl and a p-tolyl-sulphinyl substituent have been synthesized in optically pure form by intramolecular trapping of difluoroalkyl radicals on terminal double bonds. The radical intermediates have been generated by the tributyltin hydride method from 1-chloro-1,1-difluoro-3-[(4-methylphenyl)sulphinyl]hept-6-en-2-ols (4), obtained by acylating (R)-p-tolyl-omega-pentenyl sulphoxide (1) with ethyl chlorodifluoroacetate (2) and by reducing the carbonyl of the beta-ketosulphoxide intermediate 3.

引用

页码：399 / 402

页数：4

共 22 条

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