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Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates
journal contributionposted on 12.11.2013, 14:03 by Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Andrei Malkov
α to Z: Racemic α-chiral allyl boronates, which are readily synthesized from the respective primary allyl halides, undergo a highly efficient kinetic resolution in a face- and Z-selective allylation of aldehydes catalyzed by the chiral Brønsted acid (R)-TRIP (see scheme; Epin=tetraethylethylene glycol). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
The authors thank the Leverhulme Trust for the Research grant F00 261AD and LU for a studentship to C.A.I.-P. We also thank Prof. T. Kanger (Tallinn University of Technology) for access to the computational resources as part of a collaboration within COST-ORCA action CM0905.