title: Iridium-catalyzed enantioselective allylic alkylation with functionalized organozinc bromides.
abstract: Iridium-catalyzed enantioselective allylic alkylation of branched racemic carbonates with functionalized alkylzinc bromide reagents is described. Enabled by a chiral Ir/(P,olefin) complex, the method described allows allylic substitution with various primary and secondary alkyl nucleophiles with excellent regio- and enantioselectivities. The developed reaction was showcased in a concise, asymmetric synthesis of (-)-preclamol.
authors.affiliation: Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch.
authors.forename: James Y
authors.initials: JY
authors.lastname: Hamilton
authors.affiliation: Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch.
authors.forename: David
authors.initials: D
authors.lastname: Sarlah
authors.affiliation: Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch. carreira@org.chem.ethz.ch.
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
keywords: alkylation; allylic compounds; enantioselectivity; iridium; zinc