Enantioselective Synthesis of Chiral Cyclopent-2-enones by Nickel-Catalyzed Desymmetrization of Malonate Esters

Angewandte Chemie
Somnath Narayan KaradHon Wai Lam

Abstract

The enantioselective synthesis of highly functionalized chiral cyclopent-2-enones by the reaction of alkynyl malonate esters with arylboronic acids is described. These desymmetrizing arylative cyclizations are catalyzed by a chiral phosphinooxazoline/nickel complex, and cyclization is enabled by the reversible E/Z isomerization of alkenylnickel species. The general methodology is also applicable to the synthesis of 1,6-dihydropyridin-3(2H)-ones.

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Citations

Oct 3, 2018·Chemical Communications : Chem Comm·Simone M GillbardHon Wai Lam
Oct 18, 2018·Chemical Communications : Chem Comm·Heena PanchalHon Wai Lam
Sep 4, 2019·Chemical Communications : Chem Comm·Luke O'BrienHon Wai Lam
Feb 4, 2021·Chemistry : a European Journal·Harley GreenHon Wai Lam
May 6, 2021·Chemical Communications : Chem Comm·Simone M GillbardHon Wai Lam
Jun 12, 2021·Nature Chemistry·Pengwei Xu, Zhongxing Huang
Aug 28, 2020·Organic Letters·Zhijun ZhouWangqing Kong
Dec 17, 2020·The Journal of Organic Chemistry·Chada Raji ReddyRamachandra Reddy Donthiri

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