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• W2192312673 startingPage "15940" @default.
• W2192312673 abstract "Alkynyl ketones are attractive but challenging nucleophiles in enolate chemistry. Their susceptibility to other reactions such as Michael additions and the difficulty of controlling the enolate geometry make them difficult substrates. Mannich-type reactions, which previously have not been reported using N-carbamoyl-imines with simple ketone enolates, became our objective. In this report, we describe the first direct catalytic Mannich-type reaction between various ynones and N-Boc imines, whose stereocontrol presumably derives from catalyst control of enolate geometry. This method produces α-substituted β-amino ynones with excellent chemo-, diastereo-, and enantioselectivity. The products can be readily transformed into a broad range of molecular scaffolds upon further one-step transformations, demonstrating the utility of ynones as masked synthetic equivalents for a variety of unsymmetrically substituted acyclic ketones. In particular, alkynyl alkyl ketones resolve the long-standing problem of the inability to use the enolates of unsymmetrical dialkyl ketones lacking α-branching for regio- and stereoselective reactions." @default.
• W2192312673 created "2016-06-24" @default.
• W2192312673 creator A5032412691 @default.
• W2192312673 creator A5086202977 @default.
• W2192312673 date "2015-12-14" @default.
• W2192312673 modified "2023-10-13" @default.
• W2192312673 title "Broad Spectrum Enolate Equivalent for Catalytic Chemo-, Diastereo-, and Enantioselective Addition to <i>N</i>-Boc Imines" @default.
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• W2192312673 doi "https://doi.org/10.1021/jacs.5b11248" @default.
• W2192312673 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4866649" @default.
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