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- Title
Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium‐Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination.
- Authors
Chen, Ya; He, Yan‐Mei; Zhang, Shanshan; Miao, Tingting; Fan, Qing‐Hua
- Abstract
A rapid construction of enantioenriched benzo‐fused quinolizidines, indolizidines, and their analogues by ruthenium‐catalyzed asymmetric cascade hydrogenation/reductive amination of quinolinyl‐ and quinoxalinyl‐containing ketones has been developed. This reaction proceeds under mild reaction conditions, affording chiral benzo‐fused aliphatic N‐heterocyclic compounds with structural diversity in good yields (up to 95 %) with excellent diastereoselectivity (up to >20:1 dr) and enantioselectivity (up to >99 % ee). Furthermore, this catalytic protocol is applicable to the formal synthesis of (+)‐gephyrotoxin.
- Subjects
QUINOLIZIDINES; CRYSTAL structure; INDOLIZIDINES; RUTHENIUM catalysts; ASYMMETRY (Chemistry); HYDROGENATION; AMINATION
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 12, p3849
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201812647