Cobalt‐Catalyzed Enantio‐ and Diastereoselective Intramolecular Hydroacylation of Trisubstituted Alkenes

• Published in: Angewandte Chemie International Edition Vol. 56; no. 9; pp. 2449 - 2453
• Main Authors: Yang, Junfeng, Rérat, Alice, Lim, Yang Jie, Gosmini, Corinne, Yoshikai, Naohiko
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 20-02-2017; Wiley-VCH Verlag
• Edition: International ed. in English
• Subjects: Alkenes; asymmetric synthesis; Catalysis; Chemical Sciences; Cobalt; cyclizations; C−H activation; Deuterium; Enantiomers; hydroacylation; Isomers; Other; Stereochemistry; cyclizations; hydroacylation; cobalt; asymmetric synthesis; C−H activation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201611518

Enantio‐ and diastereoselective synthesis of trans‐2,3‐disubstituted indanones is achieved by intramolecular hydroacylation of 2‐alkenylbenzaldehydes bearing trisubstituted alkenyl groups under cobalt‐chiral diphosphine catalysis. Notably, a high level of enantioselectivity is induced regardless of the stereochemistry (E/Z ratio) of the alkenyl group of the starting material. Deuterium‐labeling experiments shed light on the productive reaction pathways of the E‐ and Z‐isomers.
EZ: Enantio‐ and diastereoselective synthesis of trans‐2,3‐disubstituted indanones is achieved by intramolecular hydroacylation of 2‐alkenylbenzaldehydes containing trisubstituted alkenyl groups under cobalt‐chiral diphosphine catalysis. High level of enantioselectivity is induced regardless of the stereochemistry (E/Z ratio) of the alkenyl group of the starting material.