Total stereochemical control in the addition of thiols to p-toluenesulfonylacetylene. synthesis of Z- and E-2-sulfanylvinylsulfonyl derivatives.
Alkyl and aryl sulfides react with equimolecular amounts of p-toluenesulfonylacetylene in CH3CN at 0 degrees C or rt without the use of any catalytic reagent to give good yields of Z-2-sulfanylvinylsulfonyl derivatives with total diastereoselectivity. On the other hand, in the presence of 1.1 equiv of NaH in THF, the same reaction affords the corresponding E-diastereomer also with total diastereoselectivity.
Medel
Rocío
R
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain.
Monterde
María I
MI
Plumet
Joaquín
J
Rojas
Jenny K
JK