Enantioselective synthesis of 3-methyleneindan-1-ols via a one-pot allylboration–Heck reaction of 2-bromobenzaldehydes

Calder, E. D.D. and Sutherland, A. (2015) Enantioselective synthesis of 3-methyleneindan-1-ols via a one-pot allylboration–Heck reaction of 2-bromobenzaldehydes. Organic Letters, 17(10), pp. 2514-2517. (doi: 10.1021/acs.orglett.5b01047) (PMID:25933177)

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Abstract

A novel, one-pot allylboration–Heck reaction of 2-bromobenzaldehydes has been developed for the general and efficient synthesis of 3-methyleneindan-1-ols. Modification of the one-pot procedure to include chiral Brønsted acid catalyzed allylation has allowed the preparation of these building blocks in high enantioselectivity and excellent yields.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Sutherland, Professor Andrew
Authors: Calder, E. D.D., and Sutherland, A.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Journal Abbr.:Org. Lett.
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Copyright Holders:Copyright © 2015 The Authors
First Published:First published in Organic Letters 17(10):2514-2517
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
554791EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VICE PRINCIPAL RESEARCH & ENTERPRISE
554792EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VICE PRINCIPAL RESEARCH & ENTERPRISE
554793EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VICE PRINCIPAL RESEARCH & ENTERPRISE
554794EPSRC Doctoral Training Grant 2010-14Mary Beth KneafseyEngineering & Physical Sciences Research Council (EPSRC)EP/P505534/1VICE PRINCIPAL RESEARCH & ENTERPRISE