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. 2009 Mar 5;11(5):1075-8.
doi: 10.1021/ol802860u.

Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids

Guilong Li  1 , Jon C Antilla
Affiliations

Highly enantioselective hydrogenation of enamides catalyzed by chiral phosphoric acids

Guilong Li et al. Org Lett. .

Abstract

A highly enantioselective hydrogenation of enamides catalyzed by a dual chiral-achiral acid system was developed. By employing a substoichiometric amount of a chiral phosphoric acid and acetic acid, catalyst loadings as low as 1 mol % of the chiral catalyst were sufficient to provide excellent yield and enantioselectivity of the reduction product.

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Figures

Scheme 1
Scheme 1
Figure 1
Figure 1
Phosphorous based acid catalysts
Scheme 2
Scheme 2
Function of a dual-acid catalyst system
Scheme 3
Scheme 3
Proposed mechanism for the asymmetric hydrogenation of enamides catalyzed by a dual acid system.
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References

    1. Tang W, Zhang X. Chem. Rev. 2003;103:3029. - PubMed
    2. Jaekel C, Paciello R. Chem. Rev. 2006;106:2912. - PubMed
    3. Brown JM. In: Mechanism of enantioselective hydrogenation. Handbook of Homogeneous Hydrogenation. 2007 De Vries JG, Elsevier CJ, editors. Wiley-VCH Verlag GmbH & Co. KGaA; Weinheim, Germany:

    1. For reviews, see: Ouellet G, Walji AM, Macmillan DWC. Acc. Chem. Res. 2007;40:1327.You S-L. Chemistry, an Asian journal. 2007;2:820.Connon SJ. Org. Biomol. Chem. 2007;5:3407..

    1. For reviews with considerable chiral phosphoric acid coverage see: Akiyama T, Itoh J, Fuchibe K. Adv. Synth. Catal. 2006;348:999.Connon SJ. Angew. Chem., Int. Ed. 2006;45:3909.Akiyama T. Chem. Rev. 2007;107:5744.Terada M. Chem. Commun. 2008:4097. For recent reports see: Rueping M, Nachtsheim BJ, Moreth SA, Bolte M. Angew. Chem., Int. Ed. 2008;47:593.Wang X, List B. Angew. Chem., Int. Ed. 2008;47:1119.Akiyama T, Honma Y, Itoh J, Fuchibe K. Adv. Synth. Catal. 2008;350:399.Jiao P, Nakashima D, Yamamoto H. Angew. Chem. Int. Ed. 2008;47:2411.Jiang J, Yu J, Sun X-X, Rao Q-Q, Gong L-Z. Angew. Chem., Int. Ed. 2008;47:2458.Xu S, Wang Z, Zhang X, Zhang X, Ding K. Angew. Chem., Int. Ed. 2008;47:2840.Chen X-H, Zhang W-Q, Gong L-Z. J. Am. Chem. Soc. 2008;130:5652.Enders D, Narine AA, Toulgoat F, Bisschops T. Angew. Chem., Int. Ed. 2008;47:5661.Zhang G-W, Wang L, Nie J, Ma J-A. Adv. Synth. Catal. 2008;350:1457.Cheon CH, Yamamoto H. J. Am. Chem. Soc. 2008;130:9246.Hu W, Xu X, Zhou J, Liu W-J, Huang H, Hu J, Yang L, Gong L-Z. J. Am. Chem. Soc. 2008;130:7782.Rueping M, Antonchick AP. Org. Lett. 2008;10:1731.Giera D, Sickert M, Schneider C. Org. Lett. 2008;10:4259.Cheng X, Goddard R, Buth G, List B. Angew. Chem., Int. Ed. 2008;47:5079.Sickert Marcel, Schneider Christoph. Angew. Chem., Int. Ed. 2008;47:3631.Itoh J, Fuchibe K, Akiyama T. Angew. Chem., Int. Ed. 2008;47:4016.Terada M, Soga K, Momiyama N. Angew. Chem., Int. Ed. 2008;47:4122.Rueping M, Antonchick AP. Angew. Chem., Int. Ed. 2008;47:5836.Rueping M, Theissmann T, Kuenkel A, Koenigs RM. Angew. Chem., Int. Ed. 2008;47:6798.Kang Q, Zheng X-J, You S-L. Chem. Eur. J. 2008;14:3539.Cheng X, Vellalath S, Goddard R, List B. J. Am. Chem. Soc. 2008;130:15786.Rueping M, Antonchick AP. Angew. Chem., Int. Ed. 2008;47:10090..

    1. For chiral phosphoric acid catalyzed reduction reactions, see: Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M. Org. Lett. 2005;7:3781.Hoffmann S, Seayad AM, List B. Angew. Chem., Int. Ed. 2005;44:7424.Storer RI, Carrera DE, Ni Y, MacMillan DWC. J. Am. Chem. Soc. 2006;128:84.Martin NJA, List B. J. Am. Chem. Soc. 2006;128:13368.Hoffmann S, Nicoletti M, List B. J. Am. Chem. Soc. 2006;128:13074.Rueping M, Antonchick AP, Theissmann T. Angew. Chem., Int. Ed. 2006;45:3683.Mayer S, List B. Angew. Chem., Int. Ed. 2006;45:4193.Rueping M, Antonchick AP, Theissmann T. Angew. Chem., Int. Ed. 2006;45:6751.Zhou J, List B. J. Am. Chem. Soc. 2007;129:7498.Rueping M, Antonchick AP. Angew. Chem., Int. Ed. 2007;46:4562.Guo Q-S, Du D-M, Xu J. Angew. Chem., Int. Ed. 2008;47:759.Rueping M, Theissmann T, Raja S, Bats JW. Adv. Synth. Catal. 2008;350:1001.Kang Q, Zhao Z–A, You S-L. Adv. Synth. Catal. 2007;349:1657.Kang Q, Zhao Z-A, You S-L. Org. Lett. 2008;10:2031.Martin NJA, Cheng X, List B. J. Am. Chem. Soc. 2008;130:13862..

    1. Li G, Liang Y, Antilla JC. J. Am. Chem. Soc. 2007;129:5830. - PubMed
    2. Rowland GB, Zhang H, Rowland EB, Chennamadhavuni S, Wang Y, Antilla JC. J. Am. Chem. Soc. 2005;127:15696. - PubMed
    3. Rowland GB, Rowland EB, Liang Y, Antilla JC. Org. Lett. 2007;9:2609. - PubMed
    4. Li G, Rowland GB, Rowland EB, Antilla JC. Org. Lett. 2007;9:4065. - PubMed
    5. Liang Y, Rowland EB, Rowland GB, Perman JA, Antilla JC. Chem. Commun. 2007;43:4477. - PubMed
    6. Rowland EB, Rowland GB, Rivera-Otero E, Antilla JC. J. Am. Chem. Soc. 2007;129:12084. - PubMed
    7. Li G, Fronczek FR, Antilla JC. J. Am. Chem. Soc. 2008;130:12216. - PubMed

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