Prins-pinacol spiroannulations

Autor:	Larry E. Overman, Keith P. Minor
Rok vydání:	1997
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Organic Chemistry Drug Discovery Acetal Side chain Methylenecyclohexane Organic chemistry Pinacol rearrangement Selectivity Biochemistry Medicinal chemistry
Zdroj:	Tetrahedron. 53:8927-8940
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(97)90401-4
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
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::55ca3103434970d25c6dd75f845bd9ec https://doi.org/10.1016/s0040-4020(97)90401-4 Zobrazit plný text záznamu Full Text from ScienceDirect