Chiral Primary Amine Catalyzed α‐Arylation of Simple Ketones via Asymmetric Retro‐Claisen Cleavage. Issue 71 (27th October 2022)

• Record Type: Journal Article
• Authors: Han, Yanfang; Shi, Mingying; Mi, Xueling; Luo, Sanzhong
• Is Part Of: Chemistry. Volume 28:Issue 71(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-10-27
• Subjects: α-arylation -- β-diketone -- chiral primary amine -- quinone imine -- retro-Claisen cleavage; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202202584
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Highly enantioselective α ‐arylation of simple ketones has been achieved by chiral primary amine catalyzed asymmetric retro‐Claisen cleavage of β ‐diketones. This mild organocatalytic strategy enables the construction of α ‐aryl tertiary carbon stereocenters in good yields and excellent enantioselectivities (up to 98 % ee ) with the para ‐quinone monoimines as aryl sources. Furthermore, oxidative catalytic asymmetric α ‐arylation has also been realized with free p ‐aminophenols. Abstract : C−C cleavage to arylation . Enantioselective α ‐arylation of simple aliphatic ketones has been achieved via chiral primary amine catalyzed asymmetric retro‐Claisen cleavage involving β ‐diketones and para ‐quinone monoimines that facilitates the construction of α ‐aryl tertiary carbon stereocenters in good yields and high enantioselectivities.