P. Auvray, P. Knochel, J. Normant
1988
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron
Abstract
Abstract 3-Bromo-2-t-butylsulfonyl propene 1 is able to react with a large array of nucleophiles, but also of electrophiles in the presence of a metal. We show here that the resulting functionalized vinyl sulfones can add a variety of nucleophiles like lithium organo-metallics, lithium cuprates, dimethyl malonate, or nitroalkanes, to furnish highly functionalized sulfones, in some cases with a high diastereoselectivity. The synthetic potential of 1 is illustrated by an approach to retinal structure and to various enones, and to a conjugated dienone.