Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201400333
Title: Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines
Authors: Li, W.
Jia, Q.
Du, Z.
Zhang, K.
Wang, J. 
Keywords: asymmetric synthesis
cycloadditions
enamines
heterocycles
tetrahydroisoquinoline
Issue Date: 14-Apr-2014
Citation: Li, W., Jia, Q., Du, Z., Zhang, K., Wang, J. (2014-04-14). Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines. Chemistry - A European Journal 20 (16) : 4559-4562. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201400333
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. Go cyclo! An efficient asymmetric 1,3-dipolar cycloaddition reaction catalyzed by a chiral prolinol silyl ether catalyst has been developed (see scheme). Removal of the benzamide group of the intermediates furnished the desired chiral C-1-substituted tetrahydroisoquinolines in high yields with excellent stereoselectivities. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/93074
ISSN: 15213765
DOI: 10.1002/chem.201400333
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