Diastereoselective radical hydrogenation of alpha-(1-hydroxyalkyl)vinyl sulfoxides and sulfones controlled by intramolecular hydrogen bonding

Citation
N. Mase et al., Diastereoselective radical hydrogenation of alpha-(1-hydroxyalkyl)vinyl sulfoxides and sulfones controlled by intramolecular hydrogen bonding, J ORG CHEM, 65(21), 2000, pp. 7083-7090
Citations number
60
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
7083 - 7090
Database
ISI
SICI code
0022-3263(20001020)65:21<7083:DRHOAS>2.0.ZU;2-Z
Abstract
The reaction of (S)-alpha-(1-hydroxyallryl)vinyl sulfoxides (S)-5 with alky l radicals and, tributyltin hydride gave the addition-hydrogenation product s with high diastereoselectivity, whereas the reaction with (R)-alpha-(1-hy droxyalkyl)vinyl sulfoxides (R)-5 resulted in complete recovery of the star ting sulfoxides. Stereoselective intramolecular hydrogen bonding between th e hydroxy group and the diastereotopic sulfonyl oxygen led to high diastere oselectivity in the radical reaction of alpha-(1-hydroxyethyl)vinyl sulfone 12. An important role of intramolecular hydrogen bonding on the diastereos electivity as well as the reactivity toward alkyl radicals is discussed.