Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 12, Pages 3809-3813Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812647
Keywords
cascade reactions; asymmetric hydrogenation; indolizidines; quinolizidines; reductive amination
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Funding
- National Natural Science Foundation of China [21790332, 21521002, 21473216]
- CAS [QYZDJSSW-SLH023]
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A rapid construction of enantioenriched benzo-red 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.
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