Affordable Access

Publisher Website

Asymmetric oxidation of thioethers. Optical resolution of [1,1′-binaphthalene]-2,2′-dithiol

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
30
Issue
19
Identifiers
DOI: 10.1016/s0040-4039(01)80454-8

Abstract

Abstract Almost optically pure (e.e. > 98%) [1,1′-binaphthalene]-2,2′-dithiol ( 2) is obtained by resolution of racemic 2 via the transformation of the sulfidryl functions into the corresponding thioethers 3 which are asymmetrically oxidized to diastereomeric chiral monosulfoxides 4 and then reconverted into 2. The diastereo and enantioselectivity is dependent on the structure of the thioether; i.e. the dimethylthioether 3a gives two diastereomeric sulfoxides 4a in ca. 1:1 ratio, each of them in > 98% e.e., while cyclic dithioethers 3b–d afford a single diastereomeric sulfoxide 4b–d in 46–78% e.e..

There are no comments yet on this publication. Be the first to share your thoughts.