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Synthesis 1986; 1986(6): 476-480
DOI: 10.1055/s-1986-31679
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Direct 4-Alkylation of 1,3-Cyclohexanediones via Dianionic Species

Nicola M. Berry* , Mark C. P. Darey, Laurence M. Harwood
  • *Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, U. K.
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Publication Date:
20 August 2002 (online)

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1,3-Cyclohexanediones are directly alkylated at the 4 position via dianionic species generated at - 78°C using lithium diisopropylamide/hexamethylphosphoric triamide. Acetylation of the reaction products at room temperature yields the 3-acetoxy-6-alkylcyclohex-2-enones selectively.

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