Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines. Issue 4 (9th December 2020)

• Record Type: Journal Article
• Authors: Homma, Chihiro; Takeshima, Aika; Kano, Taichi; Maruoka, Keiji
• Is Part Of: Chemical science. Volume 12:Issue 4(2021)
• Page Start: 1445
• Page End: 1450
• Publication Date: 2020-12-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc05269h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α- tert -amine moiety. Abstract : Stereoselective Mannich reactions of aldehydes with ketimines provide chiral β-amino aldehydes that bear an α- tert -amine moiety. However, the structural variation of the ketimines is limited due to the formation of inseparable E / Z isomers, low reactivity, and other synthetic difficulties. In this study, a highly diastereodivergent synthesis of hitherto difficult-to-access β-amino aldehydes that bear a chiral α- tert -amine moiety was achieved using the amine-catalyzed Mannich reactions of aldehydes with less-activated Z -ketimines that bear both alkyl and alkynyl groups.