Tetrahedron p. 8927 - 8940 (1997)
Update date:2022-07-29
Topics:
Minor, Keith P.
Overman, Larry E.
Lewis acid-promoted cyclizations of methylenecyclohexane siloxy acetals 14, 15, and 21 afford spiro[4.5]decanones 22, 25, and 29 in good yield. In all cases, exclusive pinacol rearrangement of C-1 of the original three- carbon acetal side chain is observed suggesting that pinacol rearrangement of the intermediate 9-decalyl cation occurs more rapidly than conformational equilibration. This selectivity should allow Prins-pinacol spiroannulations to be employed in a predictable fashion to construct stereochemically complex spirocycles.
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