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Asymmetric synthesis of tetrahydroquinolines through a [3+2] cycloaddition controlled by dienamine catalysis.
Chemistry. 2014 May 26; 20(22):6592-6.C

Abstract

A dienamine-mediated enantioselective 1,3-dipolar cycloaddition catalyzed by a chiral prolinol silyl ether catalyst has been developed. Removal of the benzamide group of the intermediates could furnish chiral C-1 substituted tetrahydroisoquinolines (see scheme) in high yields and excellent stereoselectivities.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Li W
Allan H. Conney Laboratory for Anticancer Research, Guangdong University of Technology, Guang Dong, 510006 (China); Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691.
Wei J
No affiliation info available
Jia Q
No affiliation info available
Du Z
No affiliation info available
Zhang K
No affiliation info available
Wang J
No affiliation info available

MeSH

AminesCatalysisCycloaddition ReactionEthersQuinolinesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

24789078

Citation

Li, Wenjun, et al. "Asymmetric Synthesis of Tetrahydroquinolines Through a [3+2] Cycloaddition Controlled By Dienamine Catalysis." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 22, 2014, pp. 6592-6.
Li W, Wei J, Jia Q, et al. Asymmetric synthesis of tetrahydroquinolines through a [3+2] cycloaddition controlled by dienamine catalysis. Chemistry. 2014;20(22):6592-6.
Li, W., Wei, J., Jia, Q., Du, Z., Zhang, K., & Wang, J. (2014). Asymmetric synthesis of tetrahydroquinolines through a [3+2] cycloaddition controlled by dienamine catalysis. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(22), 6592-6. https://doi.org/10.1002/chem.201402089
Li W, et al. Asymmetric Synthesis of Tetrahydroquinolines Through a [3+2] Cycloaddition Controlled By Dienamine Catalysis. Chemistry. 2014 May 26;20(22):6592-6. PubMed PMID: 24789078.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Asymmetric synthesis of tetrahydroquinolines through a [3+2] cycloaddition controlled by dienamine catalysis. AU - Li,Wenjun, AU - Wei,Jia, AU - Jia,Qianfa, AU - Du,Zhiyun, AU - Zhang,Kun, AU - Wang,Jian, Y1 - 2014/04/30/ PY - 2014/02/09/received PY - 2014/5/3/entrez PY - 2014/5/3/pubmed PY - 2015/5/12/medline KW - asymmetric synthesis KW - azomethine imines KW - cycloaddition KW - dienamines KW - tetrahydroisoquinolines SP - 6592 EP - 6 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 22 N2 - A dienamine-mediated enantioselective 1,3-dipolar cycloaddition catalyzed by a chiral prolinol silyl ether catalyst has been developed. Removal of the benzamide group of the intermediates could furnish chiral C-1 substituted tetrahydroisoquinolines (see scheme) in high yields and excellent stereoselectivities. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24789078/Asymmetric_synthesis_of_tetrahydroquinolines_through_a_[3+2]_cycloaddition_controlled_by_dienamine_catalysis_ DB - PRIME DP - Unbound Medicine ER -