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Issue 9, 2007
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Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones

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Abstract

The efficiency and stereoselectivity of the conjugate addition of lithium (Z)- or (E)-β-amino ester enolates, generated by lithium amide conjugate addition to an α,β-unsaturated ester or deprotonation of a β-amino ester, respectively, to a range of α,β-unsaturated acceptors has been investigated. Deprotonation of a β-amino ester with LDA, followed by conjugate addition to a chiral α,β-unsaturated oxazolidinone gives high 2,3-anti selectivity (∼90% d.e.), with hydrogenolysis and purification to homogeneity generating stereodefined trisubstituted piperidinones as single stereoisomers. Asymmetric three-component couplings of α,β-unsaturated esters and alkylidene malonates initiated by lithium amide conjugate addition proceeds with high levels of 2,3-anti stereoselectivity, with hydrogenolysis giving tetrasubstituted piperidinones.

Graphical abstract: Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones

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Publication details

The article was received on 26 Jan 2007, accepted on 27 Feb 2007 and first published on 23 Mar 2007


Article type: Paper
DOI: 10.1039/B701226H
Citation: Org. Biomol. Chem., 2007,5, 1405-1415
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    Asymmetric three- and [2 + 1]-component conjugate addition reactions for the stereoselective synthesis of polysubstituted piperidinones

    S. G. Davies, P. M. Roberts and A. D. Smith, Org. Biomol. Chem., 2007, 5, 1405
    DOI: 10.1039/B701226H

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