title: Catalytic Asymmetric Allylboration of Indoles and Dihydroisoquinolines with Allylboronic Acids: Stereodivergent Synthesis of up to Three Contiguous Stereocenters.
abstract: The catalytic asymmetric allylboration of cyclic imines with γ,γ-disubstituted allylboronic acids provides products with adjacent stereocenters in high yield and stereoselectivity. Various electrophiles, including 3,4-dihydroisoquinolines and indoles, were prenylated in a fully stereodivergent fashion by switching the E/Z geometry of the allylboronate and/or the enantiomer of the BINOL catalyst. 3-Methylindole provided products with three adjacent stereocenters with high stereoselectivity in one synthetic operation.
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden.
authors.forename: Rauful
authors.initials: R
authors.lastname: Alam
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden.
authors.forename: Colin
authors.initials: C
authors.lastname: Diner
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden.
authors.forename: Sybrand
authors.initials: S
authors.lastname: Jonker
authors.affiliation: Department of Materials and Environmental Chemistry, Stockholm University, Sweden.
authors.forename: Lars
authors.initials: L
authors.lastname: Eriksson
authors.affiliation: Department of Organic Chemistry, Stockholm University, Sweden. kalman@organ.su.se.
authors.forename: Kálmán J
authors.initials: KJ
authors.lastname: Szabó
keywords: allylboration; asymmetric catalysis; indoles; organocatalysis; stereoselectivity