Enantioselective C−H Olefination of α-Hydroxy and α-Amino Phenylacetic Acids by Kinetic Resolution

• Published in: Angewandte Chemie International Edition Vol. 55; no. 8; pp. 2856 - 2860
• Main Authors: Xiao, Kai-Jiong, Chu, Ling, Yu, Jin-Quan
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 18.02.2016; Wiley
• Subjects: Alkenes - chemistry; amino acids; Carbon - chemistry; Chemistry; Chemistry, Multidisciplinary; C−H activation; enantioselectivity; Hydrogen - chemistry; kinetic resolution; Kinetics; palladium; Phenylacetates - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; enantioselectivity; C(SP)-H BONDS; IMINO ESTERS; ACTIVATION; ASYMMETRIC-SYNTHESIS; FUSED INDOLINES; amino acids; ARYLATION; IODINATION; ARYLBORONIC ACIDS; C-H activation; kinetic resolution; palladium; CATALYZED REDUCTION; EFFICIENT; C−H activation
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.201510808

Significant progress has been made in the past decade regarding the development of enantioselective C−H activation reactions by desymmetrization. However, the requirement for the presence of two chemically identical prochiral C−H bonds represents an inherent limitation in scope. Reported is the first example of kinetic resolution by a palladium(II)‐catalyzed enantioselective C−H activation and C−C bond formation, thus significantly expanding the scope of enantioselective C−H activation reactions. Quick to react: A palladium(II)‐catalyzed enantioselective C−H olefination of racemic α‐hydroxy and α‐amino phenylacetic acids by kinetic resolution has been developed using mono‐N‐protected amino acids (MPAAs) as chiral ligands. The installation of an olefin unit can lead to a novel class of chiral mandelic acid and phenylglycine derivatives.