We 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.
Highly Stereoselective Synthesis of Z-Homoallylic Alcohols by Kinetic Resolution of Racemic Secondary Allyl Boronates†
Article first published online: 10 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 20, pages 5338–5341, May 10, 2013
How to Cite
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 . Angew. Chem. Int. Ed., 52: 5338–5341. doi: 10.1002/anie.201300709
- Issue published online: 3 MAY 2013
- Article first published online: 10 APR 2013
- Manuscript Received: 27 JAN 2013
- Leverhulme Trust. Grant Number: F00 261AD
- asymmetric synthesis;
- steric effects
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).