Polysubstituted Oxygen Heterocycles by a Reformatsky-Type Reaction/Reductive Cyclization Approach from Enantiopure β-Ketosulfoxides Françoise Colobert Sabine Choppin Leticia Ferreiro-Mederos Michel Obringer Sandra Luengo Arratta Antonio Urbano M. Carmen Carreño 10.1021/ol701670g.s006 https://acs.figshare.com/articles/journal_contribution/Polysubstituted_Oxygen_Heterocycles_by_a_Reformatsky_Type_Reaction_Reductive_Cyclization_Approach_from_Enantiopure_Ketosulfoxides/2978998 The stereoselective synthesis of tetrasubstituted tetrahydrofurans and trisubstituted tetrahydropyrans bearing a sulfoxide was achieved by reductive cyclization (Et<sub>3</sub>SiH/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. 2007-10-25 00:00:00 bromo Cyclization stereoselective synthesis Approach dioxolane ketoaldehyde Polysubstituted Oxygen Heterocycles enantiopure hydroxy ketones SiH sulfoxide trisubstituted tetrahydropyrans ketosulfoxide Enantiopure reductive cyclization tetrasubstituted tetrahydrofurans derivative diastereoselective reduction Et Ketosulfoxide