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Synlett 1998; 1998(3): 245-246
DOI: 10.1055/s-1998-1633
DOI: 10.1055/s-1998-1633
letter
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Studies on α-Alkoxyalkylation of 2-Cyclohexen-1-one with Cyclic Acetals 1. Pyridiniosilylation
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
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