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

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.

Keywords

L-(+)- and/or D-(-)-tartaric acid / Phosphite ligand / 1,4-Conjugate addition / Copper salt / Cyclic enone

References

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

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

[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.

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

[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.

[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.

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

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

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

[10] Thommen M., Blaser H. U. Phosphorus Ligands in Asymmetric Catalysis, 2008, 1457.

[11] Yan M., Yang L. W., Wong K. Y., Chan A. S. C. Chem. Commun., 1999, 1: 11.

[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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[29] Delapierre G., Constantieux T., Brunel J. M., Buono G. Eur. J. Org. Chem., 2000, 13: 2507.

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