SYNTHESIS OF ENANTIOMERICALLY PURE FLUOROCYCLOHEXANE AND GEM-CHLOROFLUOROCYCLOHEXANE DERIVATIVES

被引：6

作者：

ARNONE, A

BRAVO, P

FRIGERIO, M

VIANI, F

CAVICCHIO, G

CRUCIANELLI, M

机构：

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

[2] POLITECN MILAN,DIPARTIMENTO CHIM,I-20131 MILAN,ITALY

[3] UNIV LAQUILA,DIPARTIMENTO CHIM INGN CHIM & MAT,I-67010 LAQUILA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

gem-Chloronuorocyclohexanols 10 are prepared in good yields by radical-promoted cyclization from the corresponding omega-dichlorofluoroheptenols 4. Fluorocyclohexanols 11 are obtained either from 10 or in a single step from open-chain alcohols 4. The stereochemical outcome of both the radical cyclization and the reductive dechlorination is discussed. Elimination of the chiral auxiliary sulfinyl group and appropriate elaborations afford enantiomerically pure derivatives 12-17. Relative and absolute configurations as well as preferred conformations in solution for all final compounds are provided.

引用

页码：6448 / 6455

页数：8

共 43 条

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[2] SYNTHESIS OF OPTICALLY PURE FLUORO-CYCLOHEXANE AND GEM-CHLOROFLUORO-CYCLOHEXANE DERIVATIVES BY INTRAMOLECULAR TRAPPING OF DIHALOALKYL RADICALS [J].