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Org Biomol Chem. 2013 Sep 25;11(40):7004-10. doi: 10.1039/c3ob41328d.

Metal-free borylative ring-opening of vinyl epoxides and aziridines.

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1
Department de Química Física i Inorgànica, Univ. Rovira i Virgili, C/Marcel.lí Domingo s/n, 43007 Tarragona, Spain. mariaelena.fernandez@urv.cat.

Abstract

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 SN2' 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.

PMID:
24056986
DOI:
10.1039/c3ob41328d
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