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Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines.
Chemistry. 2014 Apr 14; 20(16):4559-62.C

Abstract

Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines were developed. The reactions between diversely substituted C,N-cyclic azomethine imines and aldehydes proceeded smoothly in the presence of chiral prolinol silyl ether catalyst and gave the C-1-substituted tetrahydroisoquinolines in a highly stereoselective manner. These tetrahydroisoquinolines could be efficiently transformed to several other useful polycyclic frameworks.

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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 (P.R. China); Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543 (Singapore), Fax: (+65) 6516-1691.
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

AldehydesAminesAzo CompoundsCatalysisCyclizationCycloaddition ReactionHeterocyclic CompoundsIminesStereoisomerismTetrahydroisoquinolinesThiosemicarbazones

Pub Type(s)

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

Language

eng

PubMed ID

24644273

Citation

Li, Wenjun, et al. "Amine-catalyzed Enantioselective 1,3-dipolar Cycloadditions of Aldehydes to C,N-cyclic Azomethine Imines." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 16, 2014, pp. 4559-62.
Li W, Jia Q, Du Z, et al. Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines. Chemistry. 2014;20(16):4559-62.
Li, W., Jia, Q., Du, Z., Zhang, K., & Wang, J. (2014). Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(16), 4559-62. https://doi.org/10.1002/chem.201400333
Li W, et al. Amine-catalyzed Enantioselective 1,3-dipolar Cycloadditions of Aldehydes to C,N-cyclic Azomethine Imines. Chemistry. 2014 Apr 14;20(16):4559-62. PubMed PMID: 24644273.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines. AU - Li,Wenjun, AU - Jia,Qianfa, AU - Du,Zhiyun, AU - Zhang,Kun, AU - Wang,Jian, Y1 - 2014/03/18/ PY - 2014/01/27/received PY - 2014/3/20/entrez PY - 2014/3/20/pubmed PY - 2015/4/18/medline KW - asymmetric synthesis KW - cycloadditions KW - enamines KW - heterocycles KW - tetrahydroisoquinoline SP - 4559 EP - 62 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 16 N2 - Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines were developed. The reactions between diversely substituted C,N-cyclic azomethine imines and aldehydes proceeded smoothly in the presence of chiral prolinol silyl ether catalyst and gave the C-1-substituted tetrahydroisoquinolines in a highly stereoselective manner. These tetrahydroisoquinolines could be efficiently transformed to several other useful polycyclic frameworks. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24644273/Amine_catalyzed_enantioselective_13_dipolar_cycloadditions_of_aldehydes_to_CN_cyclic_azomethine_imines_ DB - PRIME DP - Unbound Medicine ER -