LETTER
Stereoselective Synthesis of E-Vinyl Sulfides from Alkynes
3497
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(15) General Procedure: b-Cyclodextrin (1 mmol) was
dissolved in H2O (1 mL) by warming to 60 °C until a clear
solution was formed. Then alkyne (1 mmol) dissolved in
acetone (1 mL) was added dropwise and the mixture was
allowed to cool to r.t. Thiol (1 mmol) was then added and the
mixture was stirred at r.t. until the reaction was complete
(Table 1). The organic material was extracted with EtOAc,
the extract was dried and concentrated under reduced
pressure and the resulting product, although seen as single
compound by TLC, was further purified by passing through
a column of silica gel. The cyclodextrin was recovered by
filtration and reused.
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Synlett 2006, No. 20, 3495–3497 © Thieme Stuttgart · New York