Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium‐Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination
Authors:
- 6 December 2018
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 58 (12) , 3809-3813
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.Keywords
Funding Information
- National Natural Science Foundation of China (21790332, 21521002 and 21473216)
This publication has 84 references indexed in Scilit:
- Catalytic Asymmetric Syntheses of Quinolizidines by Dirhodium-Catalyzed Dearomatization of Isoquinolinium/Pyridinium Methylides–The Role of Catalyst and Carbene SourceJournal of the American Chemical Society, 2013
- Ruthenium–NHC‐Catalyzed Asymmetric Hydrogenation of Indolizines: Access to Indolizidine AlkaloidsAngewandte Chemie International Edition, 2013
- Ruthenium‐NHC‐katalysierte asymmetrische Hydrierung von Indolizinen: Zugang zu Indolizidin‐AlkaloidenAngewandte Chemie, 2013
- Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary AminothioureasJournal of the American Chemical Society, 2013
- Asymmetric Hydrogenation of Heteroarenes and ArenesChemical Reviews, 2011
- Asymmetric Hydrogenation of 2- and 2,3-Substituted Quinoxalines with Chiral Cationic Ruthenium Diamine CatalystsOrganic Letters, 2011
- A Convergent Stereoselective Synthesis of Quinolizidines and Indolizidines: Chemoselective Coupling of 2-Hydroxymethyl-Substituted Allylic Silanes with IminesJournal of the American Chemical Society, 2009
- Total Synthesis of Indolizidine Alkaloid (−)‐209D: Overriding Substrate Bias in the Asymmetric Rhodium‐Catalyzed [2+2+2] CycloadditionAngewandte Chemie International Edition, 2009
- Iminium ion cascade reactions: stereoselective synthesis of quinolizidines and indolizidinesTetrahedron, 2008
- Enantioselective ruthenium-mediated synthesis of (-)-indolizidine 223ABThe Journal of Organic Chemistry, 1992