LEWIS ACID-INDUCED ENE-CYCLIZATION OF OMEGA-OLEFINIC TRIFLUOROMETHYL KETONES - ACCESS TO ALICYCLIC COMPOUNDS BEARING A CF3 GROUP

被引:12
作者
ABOUABDELLAH, A
AUBERT, C
BEGUE, JP
BONNETDELPON, D
GUILHEM, J
机构
[1] CNRS,CERCOA,2 RUE H DUNANT,F-94320 THIAIS,FRANCE
[2] CNRS,ICSN,F-91198 GIF SUR YVETTE,FRANCE
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期
关键词
D O I
10.1039/p19910001397
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several catalysts (Me2AlCl, MeAlCl2, EtAlCl2 and TiCl4) for the ene carbocyclization of olefinic trifluoromethyl ketonic compounds have been compared. Thus, five-, six-, seven- and eight-membered-ring compounds were obtained. Olefin regiochemistry and stereoselectivity are better controlled than in related non-fluorinated series. High yields of cyclic trifluoromethyl alcohols were obtained by the achievement of type-I, -II or -III ene processes, concerted or otherwise. The first example of an eight-membered cyclization is described.
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页码:1397 / 1403
页数:7
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