Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 37, Pages 9659-9664Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob01523e
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- Spanish Ministerio de Economia y Competitividad (MINECO) [CTQ2013-43395P, CTQ2011-29054-C02-01]
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We have experimentally proved the unsymmetrical 1,1-diboration of diazo compounds, formed in situ from aldehydes and cyclic and non-cyclic ketones, in the absence of any transition metal complex. The heterolytic cleavage of the mixed diboron reagent, Bpin-Bdan, and the formation of two geminal C-Bpin and C-Bdan bonds has been rationalised based on DFT calculations to occur via a concerted-asynchronous mechanism. Diastereoselection is attained on substituted cyclohexanones and DFT studies provide understanding on the origin of the selectivity. The alkoxide-assisted selective deborylation of Bpin from multisubstituted sp(3)-carbon and generation of a Bdan stabilized carbanion, easily conducts a selective protodeboronation sequence.
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