ChemInform Abstract: Prins-Pinacol Spiroannulations

Autor:	Keith P. Minor, Larry E. Overman
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Acetal Side chain Methylenecyclohexane General Medicine Pinacol rearrangement Selectivity Medicinal chemistry
Zdroj:	ChemInform. 28
ISSN:	0931-7597
DOI:	10.1002/chin.199743087
Popis:	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.
Databáze:	OpenAIRE
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