ol701670g_si_006.pdf (383.8 kB)
Polysubstituted Oxygen Heterocycles by a Reformatsky-Type Reaction/Reductive Cyclization Approach from Enantiopure β-Ketosulfoxides
journal contribution
posted on 2007-10-25, 00:00 authored by Françoise Colobert, Sabine Choppin, Leticia Ferreiro-Mederos, Michel Obringer, Sandra Luengo Arratta, Antonio Urbano, M. Carmen CarreñoThe stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by
reductive cyclization (Et3SiH/TMSOTf) from the corresponding enantiopure hydroxy ketones protected as a dioxolane. These derivatives are
easily accessible from a Reformatsky-type reaction between α-bromo-α‘-sulfinyl ketones and protected α- or β-ketoaldehydes, followed by
diastereoselective reduction of the resulting β-ketosulfoxide.
History
Usage metrics
Categories
Keywords
bromoCyclizationstereoselective synthesisApproachdioxolaneketoaldehydePolysubstituted Oxygen Heterocyclesenantiopure hydroxy ketonesSiHsulfoxidetrisubstituted tetrahydropyransketosulfoxideEnantiopurereductive cyclizationtetrasubstituted tetrahydrofuransderivativediastereoselective reductionEtKetosulfoxide
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC