Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution

• Published in: Angewandte Chemie International Edition Vol. 60; no. 10; pp. 5268 - 5272
• Main Authors: Chen, Yunrong, Zhu, Chaofan, Guo, Zheng, Liu, Wei, Yang, Xiaoyu
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 01.03.2021; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: asymmetric organocatalysis; Asymmetric synthesis; Asymmetry; Catalysis; Catalysts; Chemistry; Chemistry, Multidisciplinary; Hydrazine; Hydrazines; hydroquinolines; kinetic resolution; Phosphoric acid; Physical Sciences; Protocol (computers); remote amination; Science & Technology; Substrates; Synthesis; α,α-disubstitution; asymmetric organocatalysis; remote amination; CATALYSIS; ENANTIOSELECTIVE SYNTHESIS; ISOQUINOLINES; ACYLATION; ANION-BINDING APPROACH; QUINOLINES; INDOLINES; TRANSFER HYDROGENATION; AMINES; TETRAHYDROQUINOLINES; kinetic resolution; hydroquinolines; alpha,alpha-disubstitution; α,α-disubstitution

The first kinetic resolution of hydroquinoline derivatives with α,α‐disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate‐ and enantio‐...