Photoreactions of N-alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones with L-cysteine derivatives in aqueous solutions

Photolysis of substituted N-alkoxythiazolethiones 1 in aqueous solvents furnishes alkoxyl radicals 2 which, upon stereoselective 5-exo-trig cyclization, are trapped by water soluble thiols (l-cysteine, l-cysteine ethyl ester, or the reduced form of glutathione, GSH) to afford disubstituted tetrahydr...

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 9; pp. 799 - 800
Main Authors Hartung, J, Kneuer, R, Spehar, K
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2001
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
RADICALS
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Summary:Photolysis of substituted N-alkoxythiazolethiones 1 in aqueous solvents furnishes alkoxyl radicals 2 which, upon stereoselective 5-exo-trig cyclization, are trapped by water soluble thiols (l-cysteine, l-cysteine ethyl ester, or the reduced form of glutathione, GSH) to afford disubstituted tetrahydrofurans 3 in synthetically useful yields and with satisfactory to excellent diastereoselectivities.
ISSN:1359-7345
1364-548X
DOI:10.1039/b101097m