Catalytic Asymmetric Mannich Reaction with N‐Carbamoyl Imine Surrogates of Formaldehyde and Glyoxylate. (2nd October 2017)

• Record Type: Journal Article
• Authors: You, Yang'en; Zhang, Long; Cui, Linfeng; Mi, Xueling; Luo, Sanzhong
• Is Part Of: Angewandte Chemie. Volume 129:Number 44(2017)
• Page Start: 14002
• Page End: 14006
• Publication Date: 2017-10-02
• Subjects: Aminocarbonylverbindungen -- Enamin-Katalyse -- Imin-Surrogate -- Mannich-Reaktionen -- N, O-Acetale; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201707005
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: N, O‐acetals (NOAcs) were developed as bench stable surrogates for N‐carbamoyl, (Boc, Cbz and Fmoc) formaldehyde and glyoxylate imines in asymmetric Mannich reactions. The NOAcs can be directly utilized in the chiral primary amine catalyzed Mannich reactions of both acyclic and cyclic β‐ketocarbonyls with high yields and excellent stereoselectivity. The current reaction offers a straightforward approach in the asymmetric synthesis of α‐ or β‐amino carbonyls bearing chiral quaternary centers in a practical and highly stereocontrolled manner.