4.7 Article

Copper-Catalyzed Cascade Cyclization for the Synthesis of Trifluoromethyl-Substituted Spiro-2H-azirines from 1,6-Enynes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 357, Issue 14-15, Pages 3069-3075

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201500510

Keywords

2H-azirines; cascade cyclization; copper enynes; spirocyclic skeleton

Funding

  1. National Natural Science Foundation [NSF 21272101, 21472074, 21472073]
  2. Fundamental Research Funds for Central Universities [lzujbky-2014-243]
  3. 111 Project [J1103307]
  4. Program for Changjiang Scholars, innovative Research Team in University [IRT1138]
  5. Cuiying Student Innovation Fund of Lanzhou University [CYCXJJ-2015003]

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A method for the synthesis of trifluoromethyl CF3-substituted spirocyclic compounds containing with a unique quaternary carbon center from readily available starting materials has been developed. The reaction provides a facile access to 2H-azirines via cascade cyclization. These compounds constitute a new class of functionalized synthetic intermediates, which can be used for the synthesis of various nitrogen-containing heterocycles and biologically active CF3-containing compounds.

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