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Synlett 1994; 1994(11): 958-960
DOI: 10.1055/s-1994-23063
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Radical Cyclization of Bromomethyldimethylsilyl Propargyl Ethers. Diastereoselective Synthesis of Functionalized Cyclopentanone Precursors via a (1,5) Hydrogen-Atom Transfer.

Stéphane Bogen* , Michel Journet, Max Malacria
  • *Université P. et M. Curie, Laboratoire de Chimie Organique de Synthèse, associé au CNRS, Tour 44-54, B. 229, 4, Place Jussieu 75252 - PARIS Cedex 05, FRANCE.
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Publication Date:
22 March 2002 (online)

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A (1,5) hydrogen shift, involved in the radical cyclization of acetal ω-yne compounds, led to cyclopentanone precursors in high yields. This one-pot reaction allowed the stereocontrolled formation of two contiguous stereogenic centers from two sp hybridized carbons. When a homoallylic double bond was present in the starting material, the reaction was totally chemoselective in favor of a 5-exo-trig process.

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