Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium‐Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination | Zendy

Chen Ya | Zendy; He YanMei | Zendy; Zhang Shanshan | Zendy; Miao Tingting | Zendy; Fan QingHua | Zendy

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Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium‐Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination

Author(s) -

Chen Ya,

He YanMei,

Zhang Shanshan,

Miao Tingting,

Fan QingHua

Publication year - 2019

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201812647

Subject(s) - reductive amination , ruthenium , chemistry , amination , catalysis , combinatorial chemistry , cascade , enantioselective synthesis , cascade reaction , organic chemistry , stereochemistry , chromatography

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.

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