Stereoselectivity chiral dioxetane synthesis

The contemporary trends of dioxetane chemistry include a number of fundamental and applied aspects. The fundamental aspects encompass the stereoselective synthesis and the transformations of novel chiral dioxetanes, as well as the mechanistic studies on the thermal, electron-transfer-induced and catalytic dioxetane decomposition. The emphasis lies on the elucidation of the excited-state generation in these chemiluminescent processes. 

II. STEREOSELECTIVE SYNTHESIS OF CHIRAL DIOXETANES AND THEIR TRANSFORMATIONS... 

The past decade has seen significant achievements in stereoselective synthesis, with some pertinent developments also in dioxetane chemistry. Herein, we consider the most recent and prominent advances in the stereoselective preparation of chiral dioxetanes and their transformation into building blocks for asymmetric synthesis. 

As already hinted at above, chiral dioxetanes, obtained through the highly stereoselective [2 + 2] cycloaddition of singlet oxygen to the chiral enecarbamate, provide a convenient preparation of optically active 1,2 diols as building blocks for asymmetric synthesis (Scheme 5) . Reduction of the dioxetane 2c by L-methionine, followed by release of the oxazolidinone auxiliary by NaBH4/DBU reduction, affords the enantiomerically pure like-5 diol (for additional cases, see Table 4 in Reference 19e). 

Chiral catalysts, asymmetric metal-catalyzed suHoxidations, 478-85 Chiral 1,2-dihydronaphthalenes, photooxygenation, 265-6 Chiral dioxetanes, stereoselective synthesis, 1173-8... 

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