179088-63-2Relevant academic research and scientific papers
Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration
Earnes, Jason,Fox, David J.,De Las Heras, Maria A.,Warren, Stuart
, p. 1903 - 1914 (2007/10/03)
Single enantiomers and diastereoisomers of 2- and 3-alkyl-3-phenylsulfanyl-1,8-dioxa- and 1-oxa-8-thiaspiro-[4.5]decanes can be prepared in good yield by acid-catalysed phenylsulfanyl (PhS-) migration. Either the syn-or anti-stereochemistry can be controlled by aldol reactions or by reduction of hydroxy-ketones. The Royal Society of Chemistry 2000.
Secondary and tertiary alcohols as nucleophiles in the stereospecific synthesis of substituted tetrahydrofurans by cyclisation of 1,3-diols with phenylsulfanyl migration
Eames, Jason,De Las Heras, Maria A.,Warren, Stuart
, p. 4077 - 4080 (2007/10/03)
Rearrangement of a series of 4-phenylsulfanyl-1,3-diols with TsOH gives tetrahydrofurans stereospecifically and in high yield even if the nucleophile is a secondary or tertiary alcohol. We discuss the stereochemistry and acceptable substitution patterns of the diols which will carry out this reaction and define their limits.
Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration
Eames, Jason,De Las Heras, Maria A.,Jones, Ray V. H.,Warren, Stuart
, p. 4581 - 4584 (2007/10/03)
Single enantiomers and diastereoisomers of 2- and 3-alkyl-4- phenylsulfanyl-1,8-dioxa- and 1-oxa-8-thiaspiro[4.5]decanes can be prepared in good yield by acid-catalysed phenylsulfanyl migration. Either syn or anti stereochemistry can be selected by aldol reactions or by reduction of hydroxy-ketones.
