Quaternary centers are motifs observed in many natural products and chemists have long pursued methods to control their formation. We report a novel approach to the stereoselective synthesis of 2-alkyl-2-allyl-3-cyclohexen-1-one compounds from readily available starting materials using a four step sequence: Birch reductive alkylation, acid allylation, enol ether hydrolysis and stereoselective transition metal catalyzed decarboxyallylation. Notably, the sequence provides an efficient way to synthesize complex decarboxyallylation substrates, which are often only accessible in modest yields. Overall the sequence allows for highly functionalized molecules with quaternary centers to be synthesized in good yield.

Novel synthesis of 2-alkyl-2-allyl-3-cyclohexen-1-one compounds

244th National Meeting (2012)

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