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Synthesis 2000; 2000(7): 1009-1019
DOI: 10.1055/s-2000-6301
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(Alkylthio)alkynes as Addends in the Co(0) Catalyzed Intramolecular Pauson-Khand Reaction. Substituent Driven Enhancements of Annulation Efficiency and Stereoselectivity

Brian L. Pagenkopf* , David B. Belanger, Donogh J. R. O'Mahony, Tom Livinghouse
  • *Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA; E-mail: Livinghouse@chemistry.montana.edu
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Publication Date:
31 December 2000 (online)

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Compared to terminal alkynes, (methylthio)alkynes are generally superior substrates for the thermally promoted, Co2(CO)8 catalyzed Pauson-Khand reaction of enynes and allenynes, providing enones in higher yields and with enhanced diastereoselectivity. Improvements in yield dependent upon the use of 2,2,2-trifluoroethanol as co-solvent and an apparent preference for endo selectivity with (ethoxy)alkynes are also disclosed.

annulations - carbonylations - catalysis - diastereoselectivity - sulfides