Journal
TETRAHEDRON
Volume 67, Issue 19, Pages 3524-3532Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.03.031
Keywords
Fluorinated diazocompounds; Sigmatropic rearrangement; Allenynes; Enynes; Catalysis; Carbocyclization; Heterocycles
Categories
Funding
- Russian foundation of basic research [07-03-92171, 08-03-92504]
- CNRS France
- Russian Academy of Sciences
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A new efficient access to functionalized CF3-substituted and nitrogen or sulfur-containing heterocycles has been developed directly from diazocompounds CF3C(N-2)Z (Z=CO2Me, P(O)(OEt)(2)). The method is based on the direct selective synthesis of doubly unsaturated substrates followed by metal-mediated carbocylization. The first step has been performed by Cu(II)-catalyzed [2,3]-sigmatropic rearrangement of propargyl- or/and allyl-containing sulfur and nitrogen ylides leading to fluorinated enynes, diolefins, and especially allenynes derivatives. The second step involves their carbocyclization via ring closing metathesis and Pauson-Khand reaction. (c) 2011 Elsevier Ltd. All rights reserved.
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