Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function

Ding, Pingyu;Ghosez, Léon
(2002) Tetrahedron — Vol. 58, n° 8, p. 1565-1571 (2002)

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Authors
  • Ding, PingyuUCLouvain
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
1,1-Dimethyl-3-(phenyldio)-propane 4 was deprotonated with t-BuLi, then converted to the corresponding organocuprate reagent which, in the presence of HMPA and TMSCl was added to a variety of enones to give the corresponding silylenol ethers 7. These were cyclised without purification upon acidic conditions to give the cyclopentannulation products 9. A similar result was obtained with the corresponding orthoester reagent 6. This cyclopentannulation sequence is applicable to a wide variety of enones except for those bearing substituents near the reacting centre. (C) 2002 Published by Elsevier Science Ltd.
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Ding, P., & Ghosez, L. (2002). Cyclopentannulation of enones with organocuprate reagents containing an acetal or an orthoester function. Tetrahedron, 58(8), 1565-1571. https://doi.org/10.1016/S0040-4020(01)01248-0 (Original work published 2002)