An Aza-Enolate Strategy Enables Iridium-Catalyzed Enantioselective Hydroalkenylations of Minimally Polarized Alkenes En Route to Complex N-Aryl β-Amino Acids

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2024 Aug 6

PMID 39106062

Authors

Fenglin Hong

Craig M Robertson

John F Bower

Affiliations

Soon will be listed here.

Abstract

Cationic Ir(I)-complexes modified with homochiral diphosphines promote the hydroalkenylative cross-coupling of β-(arylamino)acrylates with monosubstituted styrenes and α-olefins. The processes are dependent on the presence of an NH unit, and it is postulated that metalation of this generates an iridium aza-enolate that engages the alkene during the C-C bond forming event. The method offers high branched selectivity and enantioselectivity and occurs with complete atom economy. Diastereocontrolled reduction of the products provides β-amino acids that possess contiguous stereocenters.

Citing Articles

Heteroaryl-Directed Iridium-Catalyzed Enantioselective C-H Alkenylations of Secondary Alcohols.

Mao W, Robertson C, Bower J J Am Chem Soc. 2024; 147(1):118-124.

PMID: 39715233 PMC: 11726574. DOI: 10.1021/jacs.4c16414.

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