Synthesis of C-2-symmetric tris-thioethers via optically active mustards

Authors
Christoffers, J Rossler, U
Citation
J. Christoffers et U. Rossler, Synthesis of C-2-symmetric tris-thioethers via optically active mustards, TETRAHEDRON, 57(9), 2001, pp. 1779-1783
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
9
Year of publication
2001
Pages
1779 - 1783
Database
ISI
SICI code
0040-4020(20010225)57:9<1779:SOCTVO>2.0.ZU;2-0
Abstract
Chiral dihydroxy thioethers derived from L-mandelic and L-lactic acid are a ctivated with SOCl2, SOBr2 and by bis-trifluoroacetate formation to give op tically active mustard gas analogues. These compounds serve as substrates f or stereospecific nucleophilic substitution reactions with NaSEt and NaSPh to furnish C-2-symmetric tris-thioethers with overall inversion of configur ation. (C) 2001 Elsevier Science Ltd. All rights reserved.