Abstract
An achiral nickel complex with a Schiff base derived from glycine was alkylated with alkyl halides under conditions of asymmetric phase-transfer catalysis. The chiral tetraol (R)-BIMBOL was employed as a catalyst. The enantiomeric purity of the alkylation products was up to 88%. Subsequent decomposition of the complexes afforded the corresponding a-amino acids.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
P. J. Knerr, W. van der Donk, J. Am. Chem. Soc., 2012, 134, 7648.
P. Conti, L. Tamborini, A. Pinto, A. Blondel, P. Minoprio, A. Mozarelli, C. De Micheli, Chem. Rev., 2011, 111, 6919.
J. T. Ngo, D. A. Tirrell, Acc. Chem. Res., 2011, 44, 677.
I. N. Ugwumba, K. Ozawa, Z. Xu, F. Ely, J. Foo, A. J. Herit, C. Coppin, S. Brown, M. C. Taylor, D. L. Ollis, L. N. Mander, G. Schenk, N. E. Dixon, G. Otting, J. G. Oake- shot, C. J. Jackson, J. Am. Chem. Soc., 2011, 133, 326.
J. Paradowska, M. Stodulski, J. Mlynarski, Angew. Chem. Int. Ed., 2009, 48, 2.
M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kebeler, R. Sturmer, T. Zelinski, Angew. Chem. Int. Ed., 2004, 43, 788.
S. Matsunaga, T. Yoshino, Chem. Rev., 2011, 11, 260.
A. Viso, R. F. de la Pradilla, M. Tortosa, A. Garcia, A. Flores, Chem. Rev., 2011, 111, PR1–42.
C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry, 2007, 18, 569.
K. Maruoka, Chem. Rev., 2010, 10, 254.
X.-L. Qiu, F.-L. Qing, Eur. J. Org. Chem., 2011, 3261.
M. J. O’Donnell, Acc. Chem. Res., 2004, 37, 506.
M. J. O’Donnell, Aldrich Acta, 2001, 34, 3.
T. Hashimoto, K. Maruoka, Chem. Rev., 2007, 107, 5656.
T. Ooi, K. Maruoka, Angew. Chem. Int. Ed., 2007, 46, 4222.
T. Ooi, K. Maruoka, Aldrich Acta, 2007, 40, 77.
K. Maruoka, T. Ooi, T. Kano, Chem. Commun., 2007, 1487.
K. Maruoka, Org. Proc. Res. Dev., 2008, 12, 679.
Y. N. Belokon, K. A. Kochetkov, T. D. Churkina, N. S. Ikonnikov, A. A. Chesnokov, O. V. Larionov, I. Singh, V. S. Parmar, S. Vyscocil, H. B. Kagan, J. Org. Chem., 2000, 65, 7041.
Y. N. Belokon, Z. T. Gugkaeva, K. V. Hakobyan, V. I. Maleev, M. A. Moskalenko, V. N. Khrustalev, A. S. Sag- hyan, A. T. Tsaloev, K. K. Babievsky, Amino Acids, 2012, 43, 299.
Y. N. Belokon, N. B. Bespalova, T. D. Churkina, I. Cisarova, M. G. Ezernitskaya, S. R. Harutyunyan, R. Hrdina, H. B. Kagan, P. Kocovsky, K. A. Kochetkov, O. V. Larionov, K. A. Lyssenko, M. North, M. Polasek, A. S. Peregudov, V. V. Prisyazhnyuk, S. Vyscocil, J. Am. Chem. Soc., 2003, 125, 12860.
A. J. Gordon, R. A. Ford, The Chemist’s Companion: A Handbook of Practical Data, Techniques, and References, John Wiley and Sons, New York, 1972.
Q. Wang, X. Chen, L. Tao, L. Wang, D. Xiao, X.-Q. Yu, L. Pu, J. Org. Chem., 2007, 72, 97.
Y.-L. Zhang, Q.-H. Fan, J. Chem. Res. (S), 2005, 778.
V. A. Soloshonok, H. Ueki, J. Am. Chem. Soc., 2007, 129, 2426.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2322–2327, December, 2012.
Rights and permissions
About this article
Cite this article
Belokon, Y.N., Maleev, V.I., Samoilichenko, Y.V. et al. Phase-transfer enantioselective monoalkylation of prochiral nickel(ii) complexes catalyzed by 3,3′-bis[hydroxy(diphenyl)methyl]-1,1′-binaphthyl-2,23′-diol (BIMBOL) as a route to α-amino acids. Russ Chem Bull 61, 2344–2349 (2012). https://doi.org/10.1007/s11172-012-0329-6
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-012-0329-6