A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride.

Authors
Morgan, PE McCague, R Whiting, A
Citation
Pe. Morgan et al., A novel sulfinylation of alkenes by tosyl cyanide with titanium(IV) chloride., TETRAHEDR L, 40(26), 1999, pp. 4857-4860
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
26
Year of publication
1999
Pages
4857 - 4860
Database
ISI
SICI code
0040-4039(19990625)40:26<4857:ANSOAB>2.0.ZU;2-4
Abstract
Tosyl cyanide is activated by titanium(IV) chloride to generate a tolylsulf inyl chloride equivalent, which readily stereo- and regio-specifically adds to certain alkenes to provide beta- chlorosulfoxides. These chlorides rapi dly hydrolyse on silica gel to provide beta-hydroxysulfoxides in stereocont rolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.