192311-07-2Relevant academic research and scientific papers
Prins-pinacol spiroannulations
Minor, Keith P.,Overman, Larry E.
, p. 8927 - 8940 (2007/10/03)
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.
