Issue 30, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
07 Jun 2017
Accepted
14 Jul 2017
First published
14 Jul 2017

Org. Biomol. Chem., 2017,15, 6323-6327

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, 15, 6323 DOI: 10.1039/C7OB01382E

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