title: Selective formation of adjacent stereocenters by allylboration of ketones under mild neutral conditions.
abstract: Allylboronic acids readily react with a broad variety of ketones, affording homoallylic alcohols with adjacent quaternary and tertiary stereocenters. The reaction proceeds with very high anti stereoselectivity even if the substituents of the keto group have a similar size. α-Keto acids react with syn stereoselectivity probably due to the formation of acyl boronate intermediates. The allylation reactions proceed without added acids/bases under mild conditions. Because of this, many functionalities are tolerated even with in situ generated allylboronic acids.
authors.affiliation: Department of Organic Chemistry, Department of Inorganic and Structural Chemistry, Stockholm University , SE-106 91 Stockholm, Sweden.
authors.forename: Rauful
authors.initials: R
authors.lastname: Alam
authors.forename: Mihai
authors.initials: M
authors.lastname: Raducan
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó