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. 2008 Dec 24;130(51):17266-7.
doi: 10.1021/ja807937m.

Cyclic ketimines as superior electrophiles for NHC-catalyzed homoenolate additions with broad scope and low catalyst loadings

Michael Rommel  1 , Takeo Fukuzumi, Jeffrey W Bode
Affiliations

Cyclic ketimines as superior electrophiles for NHC-catalyzed homoenolate additions with broad scope and low catalyst loadings

Michael Rommel et al. J Am Chem Soc. .

Abstract

Cyclic sulfonyl imines derived from ketones were identified as stable and readily prepared compounds that serve as superior electrophiles for N-heterocyclic carbene (NHC)-catalyzed annulations with alpha,beta-unsaturated aldehydes to afford highly substituted gamma-lactams. Their superior reactivity and properties are highlighted by the first example of NHC-catalyzed reactions of enals with low catalyst loadings (0.5 mol %) and broad substrate scope encompassing alkyl, aryl, and heteroaromatic substituents. These findings and supporting studies suggest an alternative, ene-like mechanism rather than the catalytic generation of a catalyst-bound homoenolate equivalent.

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Figures

Scheme 1
Scheme 1
Possible reaction pathways for NHC-catalyzed annulations of enals and cyclic sulfonyl ketimines.
Scheme 2
Scheme 2
Enantioselective annulation of cyclic ketimines.
See this image and copyright information in PMC

References

    1. Weinreb SM. Top Curr Chem. 1997;190:131–184.
    1. Enders D, Niemeier O, Henseler A. Chem Rev. 2007;107:5606–5655. - PubMed
    2. Marion N, Díez-González S, Nolan SP. Angew Chem Int Ed. 2007;46:2988–3000. - PubMed
    1. He M, Bode JW. Org Lett. 2005;7:3131–3134. - PubMed
    1. Chan A, Scheidt KA. J Am Chem Soc. 2007;129:5334–5335. - PMC - PubMed
    1. Phillips EM, Reynolds TE, Scheidt KA. J Am Chem Soc. 2008;130:2416–2417. - PMC - PubMed

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