P. Auvray, P. Knochel, J. Normant
1985
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron Letters
Abstract
Abstract 3-bromo-2-(tert-butylsulfonyl)-1-propene 1 reacts in good yields with various electrophiles (aldehydes, ketones, nitriles and alkynes) in the presence of zinc metal to give unsaturated sulfones of type 4 . These compounds can further react with soft or hard nucleophiles (alkyl-, vinyl-, aryllithium compounds, a nitroparaffin or dimethylmalonate) to yield highly functionnalized sulfones of type 5 which can be readily transformed into enones or into a dienone. Thus sulfone 1 is a versatile multi-coupling reagent which is synthetically equivalent to the a 2 a 2′ synthon 8 and to the d 2 d 2′ synthons 9 and 10 .