Asymmetric Oxidation of Labeled Cyclopentane-1,2-diones: A Mechanistic Study

摘要

A Sharpless type Ti(OiPr)4 / tartaric ester / tBuOOH catalytic complex can be used to oxidize cyclopentane-1,2-diones to γ-lactone acids in high optical purity and good yields. These γ-lactone acids are valuable intermediates in the synthesis of natural products like homocitric acid, alkyl- and aryl substituted nucleoside analogues3 and can potentially be used for a variety of other applications. In order to develop an efficient process for the preparation of the abovementioned products the mechanism of the asymmetric oxidation of cyclopentane-1,2-diones was scrutinized by means of isotopic labelling and a definite reaction mechanism was established.