A Spiro Phosphamide Catalyzed Enantioselective Proton Transfer of Ylides in a Free Carbene Insertion into N−H Bonds

• Published in: Angewandte Chemie International Edition Vol. 62; no. 15; pp. e202300691 - n/a
• Main Authors: Pan, Jia‐Bin, Zhang, Xuan‐Ge, Shi, Yi‐Fan, Han, Ai‐Cui, Chen, Yu‐Jia, Ouyang, Jing, Li, Mao‐Lin, Zhou, Qi‐Lin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 03.04.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Amines; Amino acids; Asymmetric Catalysis; Brønsted Acids; Carbenes; Catalysts; Chemistry; Chemistry, Multidisciplinary; Computer applications; Enantiomers; Insertion; Intermediates; Irradiation; N−H Insertion; Organic chemistry; Phosphamides; Physical Sciences; Protons; Science & Technology; Side reactions; Bronsted Acids; PALLADIUM; Asymmetric Catalysis; ACIDITIES; ACIDS; N-H Insertion; DIAZO-COMPOUNDS; Phosphamides; Carbenes; Brønsted Acids; N−H Insertion

Free carbene readily causes multiple side reactions due to its high energy, thus its asymmetric transformation is very difficult. We present here our findings of high‐pKa Brønsted acid catalysts that enable free carbene insertion into N−H bonds of amines to prepare chiral α‐amino acid derivatives wi...