||Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates
Wakamatsu, Takamichi ,
Nagao, Kazunori ,
Ohmiya, HirohisaSawamura, Masaya
Beilstein journal of organic chemistry
2450 , 2015-12-04 , Beilstein-Institut
A copper-catalyzed conjugate addition of alkylboron compounds (alkyl-9-BBN, prepared by hydroboration of alkenes with 9-BBN-H) to alkynoates to form beta-disubstituted acrylates is reported. The addition occurred in a formal syn-hydroalkylation mode. The syn stereoselectivity was excellent regardless of the substrate structure. A variety of functional groups were compatible with the conjugate addition.