Intramolecular titanium-promoted deoxygenative cyclization to 9-substituted-1,2,3,4-tetrahydrofluorene skeleton
作者:Syun-ichi Kiyooka、Satoshi Matsumoto、Satoshi Umezu、Ryoji Fujiyama、Daisuke Kaneno
DOI:10.1016/j.tetlet.2009.12.090
日期:2010.3
The Mukaiyama aldol reaction of 2-aryl-1-cyclohexene-1-carboxaldehydes with phenyl trimethylsilyl ketene acetal unexpectedly resulted in the formation of 9-substituted-1,2,3,4-tetrahydrofluorene derivatives via a novel intramolecular titanium-promoted deoxygenative cyclization. By successive treatment of the corresponding allyl alcohols with n-butyllithium and titanium tetrachloride, the cyclization
2-芳基-1-环己烯-1-甲醛与苯基三甲基甲硅烷基乙烯酮缩醛的Mukaiyama羟醛反应意外地导致通过新型分子内钛促进的脱氧环化反应形成9-取代的1,2,3,4-四氢芴衍生物。通过用正丁基锂和四氯化钛连续处理相应的烯丙醇,可以高收率获得环化产物。