Regio- and stereoselective copper-catalyzed α, β-protoboration of allenoates: access to Z-β, γ-unsaturated β-boryl esters. Issue 16 (6th April 2022)

• Record Type: Journal Article
• Authors: Szwetkowski, Connor; Slebodnick, Carla; Santos, Webster L.
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 16(2022)
• Page Start: 3287
• Page End: 3291
• Publication Date: 2022-04-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00423b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A regio- and stereoselective copper-catalyzed allenoate borylation protocol was developed to afford Z -β, γ-unsaturated β-boryl esters without the necessity for a base or ligand additive. Abstract : A highly efficient regio- and stereoselective method for allenoate borylation has been developed. Using CuCl and bis(pinacolato)diboron in methanol, a variety of allenoates underwent β-boration and α-protonation to afford the corresponding Z -β, γ-unsaturated β-boryl esters under mild conditions with up to 81% yields.