Asymmetric α‐Allylation of Glycinate with Switched Chemoselectivity Enabled by Customized Bifunctional Pyridoxal Catalysts

• Published in: Angewandte Chemie International Edition Vol. 61; no. 17; pp. e202200850 - n/a
• Main Authors: Ma, Jiguo, Gao, Bin, Song, Guanshui, Zhang, Ruixin, Wang, Qingfang, Ye, Zi, Chen, Wen‐Wen, Zhao, Baoguo
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 19.04.2022; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Acetates; Acetic acid; Allyl compounds; Allylic Substitution; Amides; Biomimetic Catalysis; Carbonyl Catalysis; Catalysis; Catalysts; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Esters; Glutamic acid; Intermediates; Organocatalysis; Physical Sciences; Pyridoxal; Science & Technology; Stereoisomerism; Stereoselectivity; Vitamin B6; Vitamin B-6; ACTIVATED ALLYLIC ACETATES; Allylic Substitution; CONJUGATE ADDITION-ELIMINATION; ALDEHYDE CATALYSIS; Organocatalysis; GLUTAMIC-ACID DERIVATIVES; ENANTIOSELECTIVE CONSTRUCTION; Carbonyl Catalysis; BIOMIMETIC TRANSAMINATION; DIPHOSPHINE LIGANDS; AMINO-ACIDS; SYNERGISTIC CU/PD CATALYSIS; BAYLIS-HILLMAN CARBONATES; Biomimetic Catalysis; Vitamin B6

Owing to the strong nucleophilicity of the NH2 group, free‐NH2 glycinates react with MBH acetates to usually deliver N‐allylated products even in the absence of catalysts. Without protection of the NH2 group, chiral pyridoxal catalysts bearing an amide side chain at the C3 position of the naphthyl r...