Enantioselective α-Allylation of Acyclic Esters Using B(pin)-Substituted Electrophiles: Independent Regulation of Stereocontrol Elements through Cooperative Pd/Lewis Base Catalysis

Chemistry : a European Journal
W Rush Scaggs, Thomas N Snaddon

Abstract

Cooperation between a Lewis base and Pd catalyst enables the direct enantioselective α-functionalization of aryl and vinyl acetic acid esters using a bifunctional B(pin)-substituted electrophile. Critical to the success of this method was the recognition that both catalysts could control the necessary stereochemical aspects; the Lewis base catalyst controls the enantioselectivity of the reaction, whereas the Pd catalyst regulates alkenyl-B(pin) configuration. This is the first example of using cooperative catalysis to control both stereochemical features during Pd-catalyzed allylic alkylation.

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Citations

Oct 26, 2018·Chemistry : a European Journal·Danila GasperiniAndrew D Smith
Nov 30, 2018·Organic & Biomolecular Chemistry·W Rush ScaggsThomas N Snaddon
May 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jacqueline BitaiAndrew D Smith
Jan 17, 2020·Topics in Current Chemistry·Gary J KnoxThomas N Snaddon
Jun 20, 2020·Chemistry : a European Journal·Calum McLaughlin, Andrew D Smith
Oct 28, 2019·Journal of the American Chemical Society·Eduardo Nieto-SepulvedaGuy C Lloyd-Jones
Dec 29, 2020·Journal of the American Chemical Society·Byungjun KimSarah Yunmi Lee

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