Evaluating Binol-Aldehyde as a Chiral Derivatizing Agent for Diamines
Affiliation:
Department of Chemistry, University of Toronto,
80, St. George str., Toronto, Ontario M5S 3H6, Canada;
jchin@chem.utoronto.ca
DOI:
https://doi.org/10.23939/chcht09.04.417
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Abstract:
We have synthesized and tested a new binol-aldehyde compound 1, against five diamine compounds. Using 1H NMR (400 MHz) spectroscopy, stable diasteriomeric imine complexes between 1 and five diamines were formed. Chemical shift nonequivalences (up to 0.058 ppm) were obtained for imines. Linear calibration plot was obtained for determining the enantiopurity of diamines.
References:
[1] Zhang W., Loebach J., Wilson S. and Jacobsen E.: J. Am. Chem. Soc., 1990, 112, 2801.
[2] Irie R., Noda K., Ito Y. et al.: Tetrahedron: Asymmetry, 1991, 2, 481.
[3] Bennani Y. and Hanessian S.: Chem. Rev., 1997, 97, 3161.
[4] Noyori R. and Hashiguchi S.: Acc. Chem. Res., 1997, 30, 97.
[5] Jacobsen E.: Acc. Chem. Res., 2000, 33, 421.
[6] Noyori R. and Ohkuma T.: Angew. Chem. Int. Edn., 2001, 40, 40.
[7] Seiders T., Ward D. and Grubbs R.: Org. Lett., 2001, 3, 3225.
[8] Busacca C., Grossbach D., So R. et al.: Org. Lett., 2003, 5, 595.
[9] Liu Y. and Ding K.: J. Am. Chem. Soc., 2005, 127, 10488.
[10] Denmark S., Pham S., Stavenger R. et al.: J. Org. Chem., 2006, 71, 3904.
[11] Soltani O., Ariger M. and Carreira E.: Org. Lett., 2009, 11, 4196.
[12] Zhu Q., Huang H., Shi D. et al.: Org. Lett., 2009, 11, 4536.
[13] Soltani O., Ariger M., Vázquez-Villa H. and Carreira E.: Org. Lett., 2010, 12, 2893.
[14] Lu Z., Wilsily A. and Fu G.: J. Am. Chem. Soc., 2011, 133, 8154.
[15] Steward K., Corbett M., Goodman C. and Johnson J.: J. Am. Chem. Soc., 2012, 134, 20197.
[16] Steward K., Gentry E. and Johnson J.: J. Am. Chem. Soc., 2012, 134, 7329.
[17] Michalson E. and Szmuszkovicz J.: Prog. Drug. Res., 1989, 33, 135.
[18] Lucet D., Le Gall T. and Mioskowski C.: Angew. Chem. Int. Edn., 1998, 37, 2580.
[19] Saibabu Kotti S., Timmons C. and Li G.: Chem. Biol. Drug Des., 2006, 67, 101.
[20] Yang Q., Chang J., Song J. et al.: Bioorg. Med. Chem. Lett., 2013, 23, 4602.
[21] So S., Mui L., Kim H. and Chin J.: Acc. Chem. Res., 2012, 45, 1345.
[22] Ma F., Ai L., Shen X. and Zhang C.: Org. Lett., 2007, 9, 125.
[23] Ma Q., Ma M., Tian H. et al.: Org. Lett., 2012, 14, 5813.
[24] Cuevas F., Ballester P. and Pericas M.: Org. Lett., 2005, 7, 5485.
[25] Port A., Virgili A. and Jaime C.: Tetrahedron: Asymmetry, 1996, 7, 1295.
[26] Port A., Virgili A., Alvarez-Larena A. and Piniella J.: Tetrahedron: Asymmetry, 2000, 11, 3747.
[27] Enders D., Thomas C. and Runsink J.: Tetrahedron: Asymmetry, 1999, 10, 323.
[28] Yang X.-M., Wang G.-T., Zhong C. et al.: Tetrahedron: Asymmetry, 2006, 17, 916.
[29] Louzao I., Garcia R., Seco J. et al.: Org. Lett., 2009, 11, 53.
[30] Moon L., Jolly R., Kasetti Y. and Bharatam P.: Chem. Commun., 2009, 1067.
[31] Kelly A., Perez-Fuertes Y., Fossey J. et al.: Nat. Protoc., 2008, 3, 215.
[32] Perez-Fuertes Y., Kelly A., Fossey J. et al.: Nat. Protoc., 2008, 3, 210.
[33] Chin J., Kim D., Kim H.-J. et al.: Org. Lett., 2004, 6, 2591.
[34] Yang D., Li X., Fan Y. and Zhang D.: J. Amer. Chem. Soc., 2005, 127, 7996.
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