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Copper-catalyzed, stereoconvergent, cis-diastereoselective borylative cyclization of ω-mesylate-α,β-unsaturated esters and ketones

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Abstract

The Cu(I)-catalyzed stereoconvergent borylative cyclization of ω-mesylate-α,β-unsaturated compounds is facilitated by a simple Cu-bisphosphine catalyst. This reaction provides a novel route to cis-β-boron-substituted five- and six-membered carbocycle and heterocycle esters. Mechanistic studies indicate that stereoconvergence and cis-substitution likely stem from the rapid enolation of the borylcopper adduct with the substrate double bond and the formation of a five-membered intermediate, respectively.

Graphical abstract: Copper-catalyzed, stereoconvergent, cis-diastereoselective borylative cyclization of ω-mesylate-α,β-unsaturated esters and ketones

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Publication details

The article was received on 07 Jun 2017, accepted on 14 Jul 2017 and first published on 14 Jul 2017


Article type: Communication
DOI: 10.1039/C7OB01382E
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Copper-catalyzed, stereoconvergent, cis-diastereoselective borylative cyclization of ω-mesylate-α,β-unsaturated esters and ketones

    Y. Zuo, X. Chang, Z. Hao and C. Zhong, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01382E

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