Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates

Incerti-Pradillos, Celia A.; Kabeshov, Mikhail A.; Malkov, Andrei

File(s) under permanent embargo

Reason: This item is currently closed access.

Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates

journal contribution

posted on 2013-11-12, 14:03 authored by Celia A. Incerti-Pradillos, Mikhail A. Kabeshov, Andrei MalkovAndrei 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.

Funding

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.

History

School

Science

Department

Chemistry

Citation

INCERTI-PRADILLOS, C.A., KABESHOV, M.A. and MALKOV, A.V., 2013. Highly stereoselective synthesis of z-homoallylic alcohols by kinetic resolution of racemic secondary allyl boronates. Angewandte Chemie - International Edition, 52 (20), pp. 5338 - 5341

Publisher

Version

AM (Accepted Manuscript)

Publication date

2013

Notes

This article is closed access, it was published in the journal Angewandte Chemie - International Edition [ © Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim]. The definitive version is available at: http://dx.doi.org/10.1002/anie.201300709