Access to Cyclic β‐Amino Acids by Amine‐Catalyzed Enantioselective Addition of the γ‐Carbon Atoms of α, β‐Unsaturated Imines to Enals. Issue 48 (23rd October 2019)

• Record Type: Journal Article
• Authors: Luo, Guoyong; Huang, Zhijian; Zhuo, Shitian; Mou, Chengli; Wu, Jian; Jin, Zhichao; Chi, Yonggui Robin
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 48(2019)
• Page Start: 17189
• Page End: 17193
• Publication Date: 2019-10-23
• Subjects: amine catalysis -- cyclic β-amino acid -- Michael addition -- Michael donors -- remote γ carbon; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201908896
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Disclosed herein is a new catalytic approach for an efficient access to cyclic β‐amino acids widely found in bioactive small molecules and peptidic foldamers. Our method involves addition of the remote γ‐carbon atoms of α, β‐unsaturated imines to enals by iminium organic catalysis. This highly chemo‐ and stereo‐selective reaction affords cyclic β‐amino aldehydes that can be converted to amino acids bearing quaternary stereocenters with exceptional optical purities. Our study demonstrates the unique power of organic catalytic remote carbon reactions in rapid synthesis of functional molecules. Abstract : Direct vinylogous Michael addition of the remote γ‐carbon atoms of α, β‐unsaturated imines to enals is realized through iminium organic catalysis, providing a quick access to enantiopure cyclic amino acids.