Abstract

A series of novel menthone oxime ethers were synthesized in three steps starting from (–)-menthol. Analysis of the 13C NMR chemical shift differences between α carbons of oxime derivatives (O-alkyl oximes) provides a convenient and reliable means of assigning oxime stereochemistry. It has been found that carbons syn to the oxime are shifted more upfield than carbons anti to the oxime moiety. Significant E products were obtained.

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