Two homoallyl/cyclopropylalkyl rearrangements accompanying a Wolff–Kishner type reduction
作者:Manfred Schlosser、Armin Zellner
DOI:10.1016/s0040-4039(01)01127-3
日期:2001.8
study for the enantioselective synthesis of the natural product (S)-bakuchiol, the deoxygenation of a recently described trishomoallyl alcohol was attempted using the Kabalka modification of the Wolff–Kishner method after prior oxidation of the alcohol to the ketone. However, an unprecedented succession of homoallyl/cyclopropyl ring closure and ring opening altered the carbon skeleton profoundly. The
作为对天然产物(S)-巴库酚的对映选择性合成的模型研究,在先将醇先氧化为酮后,使用Wolff-Kishner方法的Kabalka修饰法尝试对最近描述的三十二烯丙基醇进行脱氧。但是,前所未有的连续的烯丙基/环丙基开环和开环过程极大地改变了碳骨架。尽管尚不能明确排除碳负离子,但假定关键中间体为自由基。