Photooxygenation 1,2-dioxetane synthesis

The oxazolidinone-substituted olefin Ic (Scheme 3) constitutes another fortunate substrate for the diastereoselective synthesis of a chiral dioxetane , which is of preparative value for the enantiomeric synthesis of 1,2 diols . For example, the photooxygenation of the enecarbamate Ic produces the asymmetric dioxetane 2c in >95% jt-facial diastereoselectivity. The attack of the O2 occurs from the jt face anti to the isopropyl... 

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

Adam, W, Griesbeck, A.G., GoUnick, K., and Knutzen-Mies, K., 1,2-Dioxetanes derived from 4,5-dimethyl-2,3-dihydrofuran synthesis via photooxygenation, activation parameters and excitation properties, /. Org. Chem., 53,1492, 1988. 

Lopez, L., Troisi, L., Rashid, S. M. K., and Schaap, A. R, Synthesis of 1,2-dioxetanes via 9,10-dicyanoanthracene sensitized chain electron-transfer photooxygenations. Tetrahedron Lett., 30, 485, 1989. 

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