Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 40, Pages 7004-7010Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob41328d
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Funding
- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2010-16226, CTQ2011-29054-C02-02]
- Generalitat de Catalunya [2009SGR-00462]
- ICIQ Foundation
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A rational approach towards the borylative ring-opening of vinylepoxides and vinylaziridines, by the in situ formed MeO--> bis(pinacolato)diboron adduct, has been developed. The enhanced nucleophilic character of the Bpin (sp(2)) moiety from the reagent favours the S(N)2' conjugated B addition with the concomitant opening of the epoxide and aziridine rings. The reaction proceeds with total chemoselectivity towards the polyfunctionalised (-OH or -NHTs) allyl boronate. Theoretical calculations have determined the transition states that come from the reaction of the vinylic substrates with the activated MeO--> bis-(pinacolato)diboron adduct, and a plausible mechanism for the organocatalytic borylative ring opening reaction has been suggested.
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