Syntheses of highly substituted enantiopure C6 and C7 enones(1).
Enantiopure epoxyvinyl sulfones SS-9a, SS-9b, produced from Jacobsen epoxidation of 2-phenylsulfonyl 1,3-cyclohexa- and cycloheptadiene, are used as a template for the construction of substituted cycloalkenones and as chiral synthetic equivalents of enones a and b. The addition of carbon nucleophiles to SS-9a, SS-9b is high yielding and stereospecific. Enantiopure alpha,beta- and gamma-substituted cycloalkenones are easily constructed using a variety of methods.
Evarts
Jerry
J
Contribution from the Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Torres
Eduardo
E
Fuchs
Philip L
PL