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Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis(boron) compounds
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Stephens, Thomas C. and Pattison, Graham (2017) Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis(boron) compounds. Organic Letters . doi:10.1021/acs.orglett.7b01474 ISSN 1523-7060.
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Official URL: http://dx.doi.org/10.1021/acs.orglett.7b01474
Abstract
We report a transition-metal-free coupling of aldehydes and ketones with geminal bis(boron) building blocks which provides the coupled, homologated carbonyl compound upon oxidation. This reaction not only extends an alkyl chain containing a carbonyl group, it also simultaneously introduces a new carbonyl substituent. We demonstrate that enantiopure aldehydes with an enolizable stereogenic center undergo this reaction with complete retention of stereochemistry.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Aldehydes, Ketones, Boron compounds | ||||
Journal or Publication Title: | Organic Letters | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 1523-7060 | ||||
Official Date: | 13 June 2017 | ||||
Dates: |
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DOI: | 10.1021/acs.orglett.7b01474 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Date of first compliant deposit: | 16 June 2017 | ||||
Date of first compliant Open Access: | 13 June 2018 | ||||
Funder: | Royal Society (Great Britain), University of Warwick Undergraduate Research Support Scheme |
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