Catalytic enantioselective intermolecular reductive aldol reaction to ketones |
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Authors: | Dongbo Zhao Masakatsu Shibasaki |
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Institution: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan |
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Abstract: | We describe the first example of a catalytic enantioselective intermolecular reductive aldol reaction. Three types of reactions were studied: (1) reactions between acetophenone and methyl acrylate; (2) reactions between symmetric ketones and β-substituted α,β-unsaturated esters; and (3) reactions between acetophenone derivatives and an allenic ester. Although only moderate enantioselectivity was obtained in the first reaction type, high to excellent enantioselectivity was realized in the enantio-induction at the α-position in the second reaction type and at the δ-position in the third reaction type. Specifically, the third reaction type afforded the corresponding tertiary alcohols with up to 99% ee. Pre-activation of the nucleophile by silyl enolate formation is not necessary in these one-pot catalytic enantioselective reductive aldol reactions. |
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Keywords: | Asymmetric catalysis Aldol reaction Ketones Copper fluoride Conjugate reduction Multi-component reaction |
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