Stephens, Thomas and Pattison, Graham (2017) Transition-metal-free homologative cross-coupling of aldehydes and ketones with geminal bis (boron) compounds. Organic Letters, 19 (13). pp. 3498-3501. ISSN 1523-7060
Full content URL: https://doi.org/10.1021/acs.orglett.7b01474
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GPTom Homologative Coupling Org Lett Final revised version.doc - Whole Document 433kB |
Item Type: | Article |
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Item Status: | Live Archive |
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.
Keywords: | Boron, ketones, homologation |
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Subjects: | F Physical Sciences > F100 Chemistry |
Divisions: | College of Science > School of Chemistry |
ID Code: | 52244 |
Deposited On: | 31 Oct 2022 14:32 |
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