Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 28, Pages 8100-8103Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201602880
Keywords
cycloaddition; hydrogen bonds; lactones; organocatalysis; synthetic methods
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Funding
- National Natural Science Foundation of China (NSFC) [21432003, 21272102, 91413107]
- Innovation Group of Gansu Province [1210RJIA002]
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Reported herein is a bifunctional-organocatalyst-mediated enantioselective inverse-electron-demand 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with azlactones. The strategy provides concise access to enantioenriched C1-substituted tetrahydroisoquinolines featuring a pyrazolidinone scaffold. Moreover, the scalability and practical utility of this protocol was well demonstrated by employing a gram-scale reaction and some representative transformations.
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