4.7 Article

N-Heterocyclic carbene-catalyzed tandem aza-benzoin/Michael reactions: on site reversal of the reactivity of N-Boc imines

Journal

CHEMICAL COMMUNICATIONS
Volume 47, Issue 1, Pages 493-495

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0cc01769h

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Funding

  1. National Natural Science Foundation of China [20732006, 20821002, 20972177]
  2. National Basic Research Program of China (973 Program) [2009CB825300]

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A tandem NHC-catalyzed aza-benzoin/Michael reaction has been developed as a method to efficiently produce dihydroindenones and pyrrolidinone-containing tricycles. The novel reaction pattern involves tert-butyl aryl(tosyl)methylcarbamates reacting as both electrophile and nucleophile on the same carbon.

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