Highly Enantioselective Direct Synthesis of Endocyclic Vicinal Diamines through Chiral Ru(diamine)-Catalyzed Hydrogenation of 2,2′-Bisquinoline Derivatives

An asymmetric hydrogenation of 2,2′‐bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo‐ and enantioselectivity (up to 93:7 dl/m...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-10, Vol.55 (41), p.12891-12894
Main Authors: Ma, Wenpeng, Zhang, Jianwei, Xu, Cong, Chen, Fei, He, Yan-Mei, Fan, Qing-Hua
Format: Article
Language:English
Subjects:
2,2′-bisquinolines
2′-bisquinolines
asymmetric catalysis
Carbenes
Chemical synthesis
Derivatives
Diamines
Enantiomers
homogeneous catalysis
Hydrogenation
Ruthenium
vicinal diamines
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Summary:An asymmetric hydrogenation of 2,2′‐bisquinoline and bisquinoxaline derivatives, catalyzed by chiral cationic ruthenium diamine complexes, was developed. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereo‐ and enantioselectivity (up to 93:7 dl/meso and >99 % ee). These chiral diamines could be easily transformed into a new class of chiral N‐heterocyclic carbenes (NHCs), which are important but difficult to access. Diamines are forever: Chiral cationic ruthenium diamine complexes were used to catalyze the asymmetric hydrogenation of bisquinoline and bisquinoxaline derivatives. A broad range of chiral endocyclic vicinal diamines were obtained in high yields with excellent diastereoselectivity and enantioselectivity. Moreover, these products could be easily transformed into a new class of chiral N‐heterocyclic carbenes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201608181