Direct Catalytic Asymmetric Mannich‐Type Reaction of α‐N3 Amide. Issue 49 (20th October 2015)

• Record Type: Journal Article
• Authors: Sun, Zhongdong; Weidner, Karin; Kumagai, Naoya; Shibasaki, Masakatsu
• Is Part Of: Chemistry. Volume 21:Issue 49(2015)
• Page Start: 17574
• Page End: 17577
• Publication Date: 2015-10-20
• Subjects: amide -- asymmetric catalysis -- azide -- enantioselective -- Mannich; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201503921
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: An α‐N3 7‐azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich‐type reaction with N ‐thiophosphinoyl imines by the action of a cooperative catalyst. The thus‐obtained highly enantioenriched anti ‐adduct was transformed into β‐amino‐α‐azido acid in high yield by simple acidic treatment. Abstract : Take it easy : An α‐N3 7‐azaindoline amide serves as a latent enolate to directly engage in an asymmetric Mannich‐type reaction with N ‐thiophosphinoyl imines by the action of a cooperative catalyst. The thus‐obtained highly enantioenriched anti ‐adduct was transformed into β‐amino‐α‐azido acid in high yield by simple acidic treatment.