Iridium-catalyzed enantioselective allylic alkylation with functionalized organozinc bromides. 2015

James Y Hamilton, and David Sarlah, and Erick M Carreira
Eidgenössische Technische Hochschule Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch.

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.

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