Nucleophilic epoxidation of γ-alkoxy dienyl sulfoxide derivatives

( E, E) and ( Z, E) γ-alkoxy dienyl sulfones undergo nucleophilic epoxidation with remarkable regio- and stereoselectivity to render syn oxiranes in a process mainly controlled by the alkoxy stereocenter. Upon epoxidation γ-hydroxy dienyl sulfoxides provide sulfinyl and sulfonyl oxiranes along with...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron Vol. 62; no. 11; pp. 2684 - 2692
Main Authors Fernández de la Pradilla, Roberto, Victoria Buergo, María, Montero, Carlos, Viso, Alma
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.03.2006
Elsevier
Subjects
Chemistry
Chemistry, Organic
Dienes
Nucleophilic epoxidation
Physical Sciences
Science & Technology
Sulfones
Sulfoxides
Nucleophilic epoxidation
Sulfoxides
Dienes
Sulfones
nucleophilic epoxidation
ALPHA,BETA-UNSATURATED KETONES
VINYL SULFOXIDES
dienes
EFFICIENT SYNTHESIS
HYDROXY 2-SULFINYL BUTADIENES
SULFUR-DIRECTED SYNTHESIS
sulfones
ACYCLIC CHIRAL ALKENES
ASYMMETRIC EPOXIDATION
OXIRANES
CONFORMATIONAL PREFERENCES
ALPHA-HYDROXY
sulfoxides
Online AccessGet full text

Cover

More Information
Summary:( E, E) and ( Z, E) γ-alkoxy dienyl sulfones undergo nucleophilic epoxidation with remarkable regio- and stereoselectivity to render syn oxiranes in a process mainly controlled by the alkoxy stereocenter. Upon epoxidation γ-hydroxy dienyl sulfoxides provide sulfinyl and sulfonyl oxiranes along with bis-epoxides formed through a Payne rearrangement that can be prevented by silylation of the OH group. Interestingly, the presence of a γ-silyloxy group can invert the stereochemical trend of the molecule affording mainly an anti epoxidation process. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.12.024