A Practical Titanium-Catalyzed Synthesis of Bicyclic Cyclopentenones and Allylic Amines
作者:Frederick A. Hicks、Scott C. Berk、Stephen L. Buchwald
DOI:10.1021/jo951763l
日期:1996.1.1
A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines is described. The process converts enyne substrates to iminocyclopentenes using 10 mol % of the air- and moisture-stable precatalyst Cp(2)TiCl(2) in the presence of n-BuLi and triethylsilyl cyanide. The resulting iminocyclopentenes can be hydrolyzed to cyclopentenones in good yields or reduced to allylic silylamines
描述了实用的钛催化的双环环戊烯酮和烯丙基胺的合成。该方法在n-BuLi和三乙基甲硅烷基氰化物存在下,使用10 mol%的空气和水分稳定的预催化剂Cp(2)TiCl(2)将烯炔基质转化为亚氨基环戊烯。所得的亚氨基环戊烯可以高产率水解为环戊烯,或用Red-Al或DIBALH还原为烯丙基甲硅烷基胺。用乙酰氯处理粗制甲硅烷基胺可以以优异的产率分离烯丙基酰胺。