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Synthesis of novel tartaric acid-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of diethylzinc to cyclic enones

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Abstract

Five novel tropos (3R,4R)- and/or (3S,4S)-N-benzyltartarimide-derived biphenylphosphite ligands were synthesized and applied in the Cu-catalyzed asymmetric conjugate addition of diethylzinc to cyclic enones with up to 75% e.e. Compared with the reported ligand 1-N-benzylpyrrolidine-3,4-bis[(R)-1,1’-binaphthyl-2,2’-diyl]phosphite-L-tartaric acid, the issue that L-(+)-tartaric acid backbone and (R)-binaphthyl showed strong matched/mismatched character was solved with these tropos ligands. It was found that the enantioselectivity was mainly controlled by the absolute configuration of N-benzyltartarimide backbone, and both enantiomers of the addition products can be obtained by simply changing the configuration of N-benzyltartarimide substituent.

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References

  1. van Leeuwen P. W. N. M., Kamer P. C. J., Claver C., Pàmies O., Diéguez M., Chem. Rev., 2011, 111(3), 2077

    Article  Google Scholar 

  2. Toma S., Csizmadiová J., Meciarová M., Šebesta R., Dalton Trans., 2014, 43(44), 16557

    Article  CAS  Google Scholar 

  3. Jiang H. Y., Feng W., Sun Y. W., Qi Q. F., Tian H. W., Liu H. L., Huang X. R., Chem. J. Chinese Universities, 2014, 35(7), 1500

    CAS  Google Scholar 

  4. Kou J. P., Lu Y. J., Luo X. Y., Li J. Z., Chem. Res. Chinese Universities, 2009, 25(4), 461

    CAS  Google Scholar 

  5. Li X. M., Ding Y. J., Jiao G. P., Li J. W., Yan L., Zhu H. J., Chem. Res. Chinese Universities, 2009, 25(5), 738

    Google Scholar 

  6. Fan B. M., Xie J. H., Zhou Z. T., Zhang Q., Tu Y. Q., Zhou Q. L., Chem. J. Chinese Universities, 2006, 27(10), 1894

    CAS  Google Scholar 

  7. Cesati III R. R., de Armas J., Hoveyda A. H., J. Am. Chem. Soc., 2004, 126(1), 96

    Article  Google Scholar 

  8. Gärtner M., Qu J. P., Helmchen G., J. Org. Chem., 2012, 77(2), 1186

    Article  Google Scholar 

  9. Degrado S. J., Mizutani H., Hoveyda A. H., J. Am. Chem. Soc., 2001, 123(4), 755

    Article  CAS  Google Scholar 

  10. Thommen M., Blaser H. U., Phosphorus Ligands in Asymmetric Catalysis, Wiley-VCH, Weinheim, 2008, 1457

    Google Scholar 

  11. Yan M., Yang L. W., Wong K. Y., Chan A. S. C., Chem. Commun., 1999, (1), 11

    Article  Google Scholar 

  12. Lipshutz B. H., Huang S. L., Leong W. W. Y., Zhong G. F., Isley N. A., J. Am. Chem. Soc., 2012, 134(49), 19985

    Article  CAS  Google Scholar 

  13. Ebisu Y., Kawamura K., Hayashi M., Tetrahedron: Asymmetry, 2012, 23(13), 959

    Article  CAS  Google Scholar 

  14. Roth P. M. C., Fletcher S. P., Org. Lett., 2015, 17(4), 912

    Article  CAS  Google Scholar 

  15. Lega M., Margalef J., Ruffo F., Pàmies O., Diéguez M., Tetrahedron: Asymmetry, 2013, 24(17), 995

    Article  CAS  Google Scholar 

  16. Bauer T., Majdecki M., Jurczak J., Tetrahedron, 2013, 69(7), 1930

    Article  CAS  Google Scholar 

  17. Magre M., Mazuela J., Diéguez M., Pàmies O., Alexakis A., Tetrahedron: Asymmetry, 2012, 23(1), 67

    Article  CAS  Google Scholar 

  18. Westmeier, J., von Zezschwitz, P., Chem. Commun., 2014, 50(100), 15897

    Article  CAS  Google Scholar 

  19. Zeng J. L., Yu S. B., Cao Z., Yang D. W., Catal. Lett., 2010, 136(4), 243

    Article  CAS  Google Scholar 

  20. Zhang H., Fang F., Xie F., Yu H., Yang G. Q., Zhang W. B., Tetrahedron Lett., 2010, 51(23), 3119

    Article  CAS  Google Scholar 

  21. Zhao Q. L., Wang L. L., Tetrahedron: Asymmetry, 2011, 22(21), 1885

    Article  CAS  Google Scholar 

  22. Xing A. P., Bai C. B., Wang L. L., Tetrahedron, 2013, 69(2), 455

    Article  CAS  Google Scholar 

  23. Wünnemann S., Fröhlich R., Hoppe D., Org Lett., 2006, 8(12), 2455

    Article  Google Scholar 

  24. Cserepi-Szucs S., Huttner G., Zsolnai L., Szolosy A., Hegedus C., Bakos J., Inorg. Chim. Acta, 1999, 296(1), 222

    Article  CAS  Google Scholar 

  25. Buisman G. J. H., Kamer P. C. J., van Leeuwen P. W. N. M., Tetrahedron: Asymmetry, 1993, 4(7), 1625

    Article  CAS  Google Scholar 

  26. Collman J. P., Zhong M., Costanzo S., Zhang C., J. Org. Chem., 2001, 66(24), 8252

    Article  CAS  Google Scholar 

  27. Alexakis A., Polet D., Rosset S., March S., J. Org. Chem., 2004, 69(17), 5660

    Article  CAS  Google Scholar 

  28. Jongsma T., Fossen M., Challa G., van Leeuwen P. W. N. M., J. Mol. Catal., 1993, 83(1), 17

    Article  CAS  Google Scholar 

  29. Delapierre G., Constantieux T., Brunel J. M., Buono G., Eur. J. Org. Chem., 2000, (13), 2507

    Article  Google Scholar 

  30. Facchetti S., Losi D., Iuliano A., Tetrahedron: Asymmetry, 2006, 17(21), 2993

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. China

    Zengbo Pang, Aiping Xing & Lailai Wang

  2. University of Chinese Academy of Sciences, Beijing, 100039, P. R. China

    Zengbo Pang & Aiping Xing

Authors
  1. Zengbo Pang
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  2. Aiping Xing
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  3. Lailai Wang
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Corresponding author

Correspondence to Lailai Wang.

Additional information

Supported by the National Natural Science Foundation of China (Nos.20773147, 21073211, 21174155).

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Pang, Z., Xing, A. & Wang, L. Synthesis of novel tartaric acid-derived chiral phosphite ligands and their application in the Cu-catalyzed conjugate addition of diethylzinc to cyclic enones. Chem. Res. Chin. Univ. 31, 756–760 (2015). https://doi.org/10.1007/s40242-015-5142-y

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  • DOI: https://doi.org/10.1007/s40242-015-5142-y

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