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Synlett 1998; 1998(3): 245-246
DOI: 10.1055/s-1998-1633
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Studies on α-Alkoxyalkylation of 2-Cyclohexen-1-one with Cyclic Acetals 1. Pyridiniosilylation

Fang Wang* , Regina Zibuck
  • *Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA
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Publication Date:
31 December 2000 (online)

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The conjugate addition of pyridine to 2-cyclohexen-1-one in the presence of TMSOTf forms a mildly nucleophilic species. This nucleophile, generated in situ, undergoes Lewis acid catalyzed aldol-type reactions with cyclic acetals. Upon β-elimination of pyridine, α-alkoxyalkylated enones are produced in a one-pot reaction.

conjugate addition - enone - cyclic acetals - ring opening