Abstract
Lewis acid-mediated reactions of acylzirconocene chlorides with aldehydes afforded α-ketols through the nucleophilic addition of an acyl anion. In reactions of acylzirconocene chlorides with α, β-enones, complete regioselectivity (1, 2- or 1, 4-addition) was attained by choosing a suitable catalytic system, that is, Pd (OAc)2-BF3- OEt2 for the 1, 4-addition, and Pd (OAc) 2-2 PPh3 or PdCl2 (PPh3) 2 for the 1, 2-addition. In the 1, 2-selective reaction, the moderately enantioselective 1, 2-addition of acyl anion to α, β-enones was achieved by the use of Pd (OAc)2-2 MOP catalyst. The Pd-catalyzed chemistry of the acylzirconocene chlorides also enabled us to bring about the formations of bicyclo [3.3.0] compounds through the reactions with ω-unsaturated α, β-enones. a-Amino ketones were formed by Yb (OTf)3- or, more interestingly, Bronsted acid-catalyzed reactions with imines. More efficient formations of the α-amino ketones have been carried out through three-component synthesis.
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