Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles

Angewandte Chemie
Kevin J SchwarzThomas N Snaddon

Abstract

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.

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Citations

Oct 26, 2018·Chemistry : a European Journal·Danila GasperiniAndrew D Smith
Feb 20, 2020·Chemical Communications : Chem Comm·Koki SuzukiMotoi Kawatsura
Jan 17, 2020·Topics in Current Chemistry·Gary J KnoxThomas N Snaddon
Nov 30, 2018·Organic & Biomolecular Chemistry·W Rush ScaggsThomas N Snaddon
Jun 20, 2020·Chemistry : a European Journal·Calum McLaughlin, Andrew D Smith
Mar 25, 2021·Journal of the American Chemical Society·Sheng Feng, Stephen L Buchwald
Oct 8, 2019·Organic Letters·Jing MengZhi-Yong Han
Dec 29, 2020·Journal of the American Chemical Society·Byungjun KimSarah Yunmi Lee
Oct 15, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yoshikazu Horino, Toshinobu Korenaga
Jan 21, 2022·Journal of the American Chemical Society·Dian-Feng Chen, Liu-Zhu Gong

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