Catalytic Enantioselective Synthesis of Secondary Allylic Alcohols from Terminal Alkynes and Aldehydes via 1-Alkenylboron Reagents
作者:Takashi Shono、Toshiro Harada
DOI:10.1021/ol1023213
日期:2010.11.19
enantioenriched secondary allylic alcohols starting from terminal alkynes and aldehydes. Hydroboration of terminal alkynes with dicyclohexylborane and subsequent reaction of the resulting alkenylboron reagents with aldehydes in the presence of a catalytic amount (5 mol %) of 3-(3,5-diphenylphenyl)-H8-BINOL and excess titanium tetraisopropoxide afforded the corresponding allylic alcohols in high enantioselectivities
已经开发了一种实用的一锅法,用于从末端炔烃和醛开始制备对映体富集的仲烯丙基醇。用二环己基硼烷对末端炔烃进行氢硼化,然后在催化量(5 mol%)的3-(3,5-二苯基苯基)-H 8 -BINOL和过量的四异丙氧基钛存在下,将所得的烯基硼试剂与醛反应,得到相应的高对映体选择性高达94%ee的烯丙醇。