Unexpected Brønsted Acid‐Catalyzed Domino Reaction of 3‐Hydroxyisoindolin‐1‐ones and N‐tert‐Butyl Hydrazones for the Synthesis of 3‐(Hydrazono)isoindolin‐1‐ones

• Published in: European journal of organic chemistry Vol. 2018; no. 47; pp. 6733 - 6737
• Main Authors: Chen, Hui‐Xuan, Li, Yongsu, He, Xuefeng, Zhang, Yaqi, He, Wenhuan, Liang, Hao, Zhang, Yuyang, Jiang, Xiaoding, Chen, Xiangmeng, Cao, Rihui, Liu, Gao‐Feng, Qiu, Liqin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 19.12.2018; Wiley Subscription Services, Inc
• Subjects: Acids; Aza‐Mannich reaction; Cascade chemical reactions; Catalysis; Chemical synthesis; Chemistry; Chemistry, Organic; Domino reactions; Homogeneous catalysis; Hydrazones; Isoindolinones; Organocatalysis; Phosphoric acid; Physical Sciences; Science & Technology; DIRECTING GROUP; Isoindolinones; ENANTIOSELECTIVE SYNTHESIS; AMINO ESTERS; ACYL KETIMINES; Organocatalysis; C-H ACTIVATION; ASYMMETRIC ORGANOCATALYTIC SYNTHESIS; MICHAEL ADDITION; Aza-Mannich reaction; 3+2 ANNULATION; CHIRAL DICARBOXYLIC-ACID; CARBONYLATION; Homogeneous catalysis; Domino reactions
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201801293

A Brønsted acid‐catalyzed aza‐Mannich reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones was developed. Under the catalysis of the racemic phosphoric acid or trifluoroacetic acid and mild reaction conditions, this domino reaction allows for efficient synthesis of 3‐(hydrazono)isoindolin‐1‐one derivatives in excellent yields with high chemoselectivities. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction of 5w. 3‐(Hydrazono)isoindolin‐1‐one derivatives were synthesized in excellent yields and high chemoselectivities by a Brønsted acid‐catalyzed domino reaction between 3‐hydroxyisoindolin‐1‐ones and N‐tert‐butyl hydrazones. The E‐configuration of the hydrazone products was determined by X‐ray single‐crystal diffraction.