A STEREOSELECTIVE APPROACH TO 2,6-DISUBSTITUTED TETRAHYDROPYRANS BY CONJUGATE ADDITION-REACTIONS OF VINYL SULFONES

Authors
CRAIG DC EDWARDS GL MULDOON CA
Citation
Dc. Craig et al., A STEREOSELECTIVE APPROACH TO 2,6-DISUBSTITUTED TETRAHYDROPYRANS BY CONJUGATE ADDITION-REACTIONS OF VINYL SULFONES, Synlett, (11), 1997, pp. 1318
Citations number
17
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
11
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):11<1318:ASAT2T>2.0.ZU;2-2
Abstract
A highly stereoselective synthesis of cis-2,6-disubstituted tetrahydro pyrans from functionalised 5-hexen-1-ols has been developed. Free radi cal addition of para-toluenesulfonyl iodide to the hexenol and DBU-med iated elimination of HI from the intermediate beta-iodosulfones gives vinyl sulfones: subsequent conjugate addition of the potassium alkoxid e leads to a highly stereoselective (greater than or equal to 30:1) cy clisation.