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- W2013874712 abstract "In spite of the many catalytic methodologies available for the asymmetric functionalization of carbonyl compounds at their α and β positions, little progress has been achieved in the enantioselective carbon–carbon bond formation γ to a carbonyl group. Here, we show that primary amine catalysis provides an efficient way to address this synthetic issue, promoting vinylogous nucleophilicity upon selective activation of unmodified cyclic α,β-unsaturated ketones. Specifically, we document the development of the unprecedented direct and vinylogous Michael addition of β-substituted cyclohexenone derivatives to nitroalkenes proceeding under dienamine catalysis. Besides enforcing high levels of diastereo- and enantioselectivity, chiral primary amine catalysts derived from natural cinchona alkaloids ensure complete γ-site selectivity: The resulting, highly functionalized vinylogous Michael adducts, having two stereocenters at the γ and δ positions, are synthesized with very high fidelity. Finally, we describe the extension of the dienamine catalysis-induced vinylogous nucleophilicity to the asymmetric γ-amination of cyclohexene carbaldehyde." @default.
- W2013874712 created "2016-06-24" @default.
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- W2013874712 date "2010-06-21" @default.
- W2013874712 modified "2023-10-18" @default.
- W2013874712 title "Direct asymmetric vinylogous Michael addition of cyclic enones to nitroalkenes via dienamine catalysis" @default.
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- W2013874712 doi "https://doi.org/10.1073/pnas.1001150107" @default.
- W2013874712 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2996419" @default.
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