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Syntheses of highly substituted enantiopure C6 and C7 enones(1)
Jerry Evarts1, Eduardo Torres, Philip L Fuchs
1Contribution from the Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
Abstract:
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.
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