Work

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

Year: 2018

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201805578

Authors: Somnath Narayan Karad, Heena Panchal, Christopher Clarke, William Lewis, Hon Wai Lam

Institution: University of Nottingham

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $3,033

Funders: GlaxoSmithKline, University of Nottingham, Engineering and Physical Sciences Research Council, H2020 Marie Skłodowska-Curie Actions