title: Phosphine-catalyzed anti-carboboration of alkynoates with alkyl-, alkenyl-, and arylboranes.
abstract: We found that trialkylphosphine organocatalysts promoted unprecedented anti-carboboration of alkynoates with alkyl-, alkenyl-, or arylboranes to form β-boryl acrylates. The regioselectivity of the carboboration across the polar C-C triple bond exhibited inverse electronic demand, with the less electronegative B atom being delivered to the positively charged β carbon atom. The regioselectivity and the anti stereoselectivity were both complete and robust. In addition, the substrate scope was broad with excellent functional group compatibility.
authors.affiliation: Department of Chemistry, Faculty of Science, Hokkaido University , Sapporo 060-0810, Japan.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Nagao
authors.forename: Hirohisa
authors.initials: H
authors.lastname: Ohmiya
authors.forename: Masaya
authors.initials: M
authors.lastname: Sawamura