One-pot asymmetric synthesis of alkylidene 1-alkylindan-1-ols using Brønsted acid and palladium catalysis

Faggyas, R. J., Calder, E. D.D., Wilson, C. and Sutherland, A. (2017) One-pot asymmetric synthesis of alkylidene 1-alkylindan-1-ols using Brønsted acid and palladium catalysis. Journal of Organic Chemistry, 82(21), pp. 11585-11593. (doi: 10.1021/acs.joc.7b02287) (PMID:28985675)

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Abstract

A one-pot catalytic enantioselective allylboration/Mizoroki–Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Brønsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki–Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Wilson, Dr Claire and Sutherland, Dr Andrew and Faggyas, Réka
Authors: Faggyas, R. J., Calder, E. D.D., Wilson, C., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:American Chemical Society
ISSN:0022-3263
ISSN (Online):1520-6904
Published Online:06 October 2017
Copyright Holders:Copyright © 2017 American Chemical Society
First Published:First published in Journal of Organic Chemistry 82(21): 11585-11593
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
554794EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/P505534/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE