Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 16, Pages 4559-4562Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201400333
Keywords
asymmetric synthesis; cycloadditions; enamines; heterocycles; tetrahydroisoquinoline
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Funding
- National University of Singapore [R143000532112, NRF-CRP7-2010-03]
- Guangdong University of Technology (China)
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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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