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. 2011 Feb 11;50(7):1678-82.
doi: 10.1002/anie.201005908. Epub 2011 Jan 14.

Lewis acid activated synthesis of highly substituted cyclopentanes by the N-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Daniel T Cohen  1 , Benoit Cardinal-David, Karl A Scheidt
Affiliations

Lewis acid activated synthesis of highly substituted cyclopentanes by the N-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Daniel T Cohen et al. Angew Chem Int Ed Engl. .
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Figures

Scheme 1
Scheme 1
NHC/Lewis acid homoenolate strategy.
Scheme 2
Scheme 2
Proposed reaction pathway.
Scheme 3
Scheme 3
Synthetic transformations: a) LiAlH4, THF, 0–25 °C; b) NaIO4·SiO2, CH2Cl2, 25 °C; c) NaBH4, THF/MeOH (2:1), 0 °C. d) NaIO4·SiO2, CH2Cl2, 25 °C; e) DMSO/H2O, 130 °C. DMSO = di-methyl sulfoxide.
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References

    1. Enders D, Grondal C, Hüttl MRM. Angew. Chem. 2007;119:1590.; Angew. Chem. Int. Ed. 2007;46:1570.; Almasi D, Alonso DA, Nájera C. Tetrahedron: Asymmetry. 2007;18:299.; Erkkilä A, Majander I, Pihko PM. Chem. Rev. 2007;107:5416.; Grondal C, Jeanty M, Enders D. Nat. Chem. 2010;2:167.; for selected examples, see: Rendler S, MacMillan DWC. J. Am. Chem. Soc. 2010;132:5027.; Jones SB, Simmons B, MacMillan DWC. J. Am. Chem. Soc. 2009;131:13606.

    1. Enders D, Balensiefer T. Acc. Chem. Res. 2004;37:534. - PubMed
    2. Nair V, Bindu S, Sreekumar V. Angew. Chem. 2004;116:5240. - PubMed
    3. Angew. Chem. Int. Ed. 2004;43:5130. - PubMed
    4. Zeitler K. Angew. Chem. 2005;117:7674.
    5. Angew. Chem. Int. Ed. 2005;44:7506. - PubMed
    6. Marion N, Diez-González S, Nolan SP. Angew. Chem. 2007;119:3046. - PubMed
    7. Angew. Chem. Int. Ed. 2007;46:2988. - PubMed
    8. Enders D, Niemeier O, Henseler A. Chem. Rev. 2007;107:5606. - PubMed
    9. Zeitler K. In: Organocatalysis. Reetz MT, List B, Jaroch S, Weinmann H, editors. Springer; Heidelberg: 2008. pp. 183–206.
    10. Glorius F, Hirano K. In: Organocatalysis. Reetz MT, List B, Jaroch S, Weinmann H, editors. Springer; Heidelberg: 2008. pp. 183–206.
    11. Phillips EM, Chan A, Scheidt KA. Aldrichimica Acta. 2009;42:55. - PMC - PubMed
    1. Seebach D. Angew. Chem. 1979;91:259.
    2. Angew. Chem. Int. Ed. Engl. 1979;18:239.

    1. For a recent review of methodology for the generation of homoenolates with NHCs, see: Nair V, Vellalath S, Babu BP. Chem. Soc. Rev. 2008;37:2691.

    1. Burstein C, Glorius F. Angew. Chem. 2004;116:6331.; Angew. Chem. Int. Ed. 2004;43:6205.; Sohn SS, Rosen EL, Bode JW. J. Am. Chem. Soc. 2004;126:14370.; Chan A, Scheidt KA. Org. Lett. 2005;7:905.; He M, Bode JW. Org. Lett. 2005;7:3131.; Burstein C, Tschan S, Xie XL, Glorius F. Synthesis. 2006:2418.; Phillips EM, Wadamoto M, Chan A, Scheidt KA. Angew. Chem. 2007;119:3167.; Angew. Chem. Int. Ed. 2007;46:3107.; Chan A, Scheidt KA. J. Am. Chem. Soc. 2007;129:5334.; Wadamoto M, Phillips EM, Reynolds TE, Scheidt KA. J. Am. Chem. Soc. 2007;129:10098.; Chan A, Scheidt KA. J. Am. Chem. Soc. 2008;130:2740.; Phillips EM, Reynolds TE, Scheidt KA. J. Am. Chem. Soc. 2008;130:2416.; Maki BE, Chan A, Scheidt KA. Synthesis. 2008:1306.; Nair V, Babu BP, Vellalath S, Varghese V, Raveendran AE, Suresh E. Org. Lett. 2009;11:2507.; for a recent report on the use of NHCs as Brønsted base catalysts, see: Phillips EM, Riedrich M, Scheidt KA. J. Am. Chem. Soc. 2010;132:13179.

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