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.

Diels-Alder reactions of masked o-benzoquinones: new experimental findings and a theoretical study of the inverse electron demand case.

Diels-Alder reactions of the masked o-benzoquinone (MOB) 2 with vinylene carbonate (3), the bicyclic derivatives 4, 5, and 6, and the intramolecular version of the 2-hydroxymethylfuran-MOB Diels-Alder reaction are described. In addition, a theoretical study of the Diels-Alder reactions of MOBs with enol and thioenol ethers is presented.

Domino metathesis of 2-azanorbornenones: a new strategy for the enatioselective synthesis of 1-azabicyclic compounds.

Domino metathesis of N-alkylated derivatives of (1S)-2-azanorborn-5-en-3-one allowed for the enantioselective synthesis of pyrrolizidine, quinolizidine, pyrrolidinoazepine, and pyrrolidinoazocine derivatives in a straightforward process.