Elsevier

Tetrahedron Letters

Volume 54, Issue 47, 20 November 2013, Pages 6358-6362
Tetrahedron Letters

Highly stereoselective anti-aldol reactions catalyzed by simple chiral diamines and their unique application in configuration switch of aldol products

https://doi.org/10.1016/j.tetlet.2013.09.053Get rights and content

Abstract

Chiral derivatives of trans-1,2-diaminocyclohexane with different N,N-dialkyl groups in well-defined orientations have been synthesized, and applied as catalysts for the asymmetric aldol reaction between a variety of aldehydes and ketones. Enantiomeric catalyst 1j catalyzed the reaction in ethanol and provided excellent diastereoselectivity and enantioselectivity. Significantly, simple replacement of organic solvents with water switched the products of the aldol reactions from anti to syn configuration. Such catalytic reactions led to the products with anti to syn diastereoselectivity up to 99:1 in ethanol, while in water gave the products with syn to anti diastereoselectivity up to 99:1.

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Acknowledgments

The work is supported by the National Natural Science Foundation of China (Project No.21271041) for financial aids to this work. Li would like to thank the Scientific Research Innovation Project for College Graduates of Jiangsu Province (Project CXZZ12-0118).

References and notes (14)

  • P. Guillaume et al.

    Org. Lett.

    (2010)
    P.X. Zhou et al.

    Org. Biomol. Chem.

    (2011)
    K. Takuya et al.

    Eur. J. Org. Chem.

    (2011)
  • T. Bach

    Angew. Chem., Int. Ed.

    (1994)
    S.G. Nelson

    Tetrahedron: Asymmetry

    (1998)
    T.D. Machajewski et al.

    Angew. Chem., Int. Ed.

    (2000)
    K. Fujii et al.

    Org. Lett.

    (2003)
    J.R. Chen et al.

    Org. Lett.

    (2005)
    X.Y. Xu et al.

    Org. Lett.

    (2007)
    V. Maya et al.

    Org. Lett.

    (2007)
    G. Guillena et al.

    J. Org. Chem.

    (2008)
    S. Bertelsen et al.

    Chem. Soc. Rev.

    (2009)
  • Z. Tang et al.

    J. Am. Chem. Soc.

    (2003)
    S. Saito et al.

    Acc. Chem. Res.

    (2004)
    M. Benaglia et al.

    Adv. Synth. Catal.

    (2001)
    H. Yang et al.

    J. Org. Chem.

    (2010)
    B. Lygo et al.

    Tetrahedron

    (2011)
    R. Panagiota et al.

    Tetrahedron

    (2012)
  • B. List et al.

    J. Am. Chem. Soc.

    (2000)
    K. Sakthivel et al.

    J. Am. Chem. Soc.

    (2001)
  • Y. Okuyama et al.

    Tetrahedron Lett.

    (2009)
    Y.Y. Wu et al.

    Org. Lett.

    (2006)
  • E.F. Douglas et al.

    J. Am. Chem. Soc.

    (2005)
    K. Nakayama et al.

    J. Am. Chem. Soc.

    (2008)
    G.D. Chen et al.

    J. Organomet. Chem.

    (2012)
    M. Raj et al.

    Adv. Synth. Catal.

    (2009)
    X. Zhu et al.

    Chem. Eur. J.

    (2011)
    Y. Yang et al.

    Adv. Synth. Catal.

    (2010)
    J. Nie et al.

    J. Fluorine Chem.

    (2011)
  • T. Mukaiyama

    Org. React.

    (1982)
    H. Gr€oger et al.

    Chem. Eur. J.

    (1998)
    L.W. Xu et al.

    Chem. Commun.

    (2009)
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