Experimental and Theoretical Investigations into the Stereoselectivities of Peracid Promoted Epoxidations of Substituted Norbornenes and Norbornadienes.

Abstract MCPBA promoted diastereoselective epoxidations of functionalized norbornenes and norbornadienes have been performed. The experimental results thereby obtained have been evaluated by using semiempirical (AM1) quantum chemical modeling. The AM1 computational results are consistent with experiment and correctly predict the major product of all MCPBA promoted epoxidations studied herein. Product characterization was assisted via the results of X-ray crystallographic structural analysis in the case of 10a and by comparison of calculated vs. experimental 13C NMR chemical shifts of the cyclopropyl carbon atoms in 12a and 12b.