Stereoselective synthesis of medium-sized cyclic ethers by sequential ring-closing metathesis and Tsuji–Trost allylation

Skardon-Duncan, J., Sparenberg, M., Bayle, A., Alexander, S. and Clark, J. S. (2018) Stereoselective synthesis of medium-sized cyclic ethers by sequential ring-closing metathesis and Tsuji–Trost allylation. Organic Letters, 20(9), pp. 2782-2786. (doi:10.1021/acs.orglett.8b01082) (PMID:29676923)

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Abstract

Fully functionalized medium-sized cyclic ethers, of the type found in fused polyether natural products, have been prepared by sequential ring-closing diene metathesis, conversion of the resulting cyclic enone into an allylic enol carbonate, and Tsuji–Trost allylation using a chiral palladium complex. Very high levels of diastereocontrol, favoring the diastereomer in which there is a cis relationship between the allyl group at C-2 of the medium-ring ether and the substituent at C-7/C-8, are obtained in cases where catalyst control and substrate control are matched.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Alexander, Mr Samuel and Clark, Professor Stephen and Skardon-Duncan, James
Authors: Skardon-Duncan, J., Sparenberg, M., Bayle, A., Alexander, S., and Clark, J. S.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:20 April 2018
Copyright Holders:Copyright © 2018 American Chemical Society
First Published:First published in Organic Letters 20(9):2782-2786
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 and Physical Sciences Research Council (EPSRC)EP/P505534/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
678901EPSRC DTG 2014Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M506539/1RSI - RESEARCH STRATEGY & INNOVATION
678901EPSRC DTG 2014Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M506539/1RSI - RESEARCH STRATEGY & INNOVATION
642131Doctoral Training Grant 2013 - 2017Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/L50497X/1RSI - RESEARCH STRATEGY & INNOVATION
701101EPSRC 2015 DTPMary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/M508056/1RSI - RESEARCH STRATEGY & INNOVATION