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The highly catalytic asymmetric α-hydroxylation of 1-tetralone-derived β-keto esters and β-keto amides using tert-butyl hydroperoxide (TBHP) as the oxidant was realized by a chiral N, N′-dioxide-magnesium ditriflate [Mg(OTf)2] complex. A series of corresponding chiral α-hydroxy dicarbonyl compounds was obtained in excellent yields (up to 99%) with excellent enantioselectivities (up to 98% ee). The products were easily transformed into useful building blocks and the precursor of daunomycin was achieved in an asymmetric catalytic way for the first time. [ABSTRACT FROM AUTHOR]

Chiral N,N-dioxide magnesium complexes are described as efficient catalysts for the α-hydroxylation of cyclic 1-tetralone derived β-keto esters. [ABSTRACT FROM AUTHOR]