Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration

Authors
Eames, J Fox, DJ de las Heras, MA Warren, S
Citation
J. Eames et al., Stereochemically controlled synthesis of 1,8-dioxaspiro[4.5]decanes and 1-oxa-8-thiaspiro[4.5]decanes by phenylsulfanyl migration, J CHEM S P1, (12), 2000, pp. 1903-1914
Citations number
34
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
12
Year of publication
2000
Pages
1903 - 1914
Database
ISI
SICI code
1470-4358(2000):12<1903:SCSO1A>2.0.ZU;2-8
Abstract
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 hyd roxy-ketones.