Tags

Type your tag names separated by a space and hit enter

Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination.
Angew Chem Int Ed Engl. 2019 03 18; 58(12):3809-3813.AC

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.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Chen Y
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.
He YM
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Zhang S
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Miao T
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China.
Fan QH
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), University of Chinese Academy of Sciences, Beijing, 100190, P. R. China. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

30523655

Citation

Chen, Ya, et al. "Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues Via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination." Angewandte Chemie (International Ed. in English), vol. 58, no. 12, 2019, pp. 3809-3813.
Chen Y, He YM, Zhang S, et al. Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. Angew Chem Int Ed Engl. 2019;58(12):3809-3813.
Chen, Y., He, Y. M., Zhang, S., Miao, T., & Fan, Q. H. (2019). Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. Angewandte Chemie (International Ed. in English), 58(12), 3809-3813. https://doi.org/10.1002/anie.201812647
Chen Y, et al. Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues Via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. Angew Chem Int Ed Engl. 2019 03 18;58(12):3809-3813. PubMed PMID: 30523655.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid Construction of Structurally Diverse Quinolizidines, Indolizidines, and Their Analogues via Ruthenium-Catalyzed Asymmetric Cascade Hydrogenation/Reductive Amination. AU - Chen,Ya, AU - He,Yan-Mei, AU - Zhang,Shanshan, AU - Miao,Tingting, AU - Fan,Qing-Hua, Y1 - 2019/01/09/ PY - 2018/11/04/received PY - 2018/12/14/pubmed PY - 2018/12/14/medline PY - 2018/12/8/entrez KW - asymmetric hydrogenation KW - cascade reactions KW - indolizidines KW - quinolizidines KW - reductive amination SP - 3809 EP - 3813 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 58 IS - 12 N2 - 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. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/30523655/Rapid_Construction_of_Structurally_Diverse_Quinolizidines_Indolizidines_and_Their_Analogues_via_Ruthenium_Catalyzed_Asymmetric_Cascade_Hydrogenation/Reductive_Amination_ DB - PRIME DP - Unbound Medicine ER -