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