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Stereoselective a-Oxyfunctionalisation of Benzo(hetera)cyclanones by Dimethyldioxirane.
* 1 , 2 , 1 , * 1
1  Department of Organic Chemistry, Lajos Kossuth University, H-4010 Debrecen P.O.B. 20, Hungary
2  ICN-Hungary, H-4440 Tiszavasvari, Hungary

Abstract: a-Hydroxy ketones including their cyclic derivatives are important synthetic building blocks. Chiral, non-racemic a-hydroxy ketones (and esters) are widespread in natural products. Therefore, there is a high demand to develop efficient methods for the construction of their enantiopure or at least enantiomerically enriched representatives and a number of procedures have been published in the last decades [1,2]. Our interest in the synthesis of a-hydroxy benzo(hetera)cyclanones, particularly 3-hydroxychromanones, prompted us to investigate the synthetic utility of the recently developed electrophilic chiral oxidizing system, namely dimethyldioxirane (DMD)/Jacobsen's catalyst [3] in the oxyfunctionalization of enol derivatives. Enol acetates were choosen as prochiral substrates because their higher stability as compared to silyl enol ethers and their high reactivity toward DMD
Keywords: n/a