Abstract
A reaction of triethyl phosphite with 3-alkyl-1-phenylnaphthoxazines in the presence of halotrimethylsilanes with subsequent removal of the trimethylsilyl group by hydrolysis furnished diastereomeric α-aminoalkylphosphonic derivatives of Betti base. The highest diastereomeric excess was observed in the reaction with bromotrimethylsilane at low temperature. In the case of 3-isobutyl-1-phenylnaphthoxazine, a major diastereomer was isolated from the reaction mixture by crystallization. X-ray diffraction analysis was used to establish relative configuration of its chiral centers. This method can be also used for the preparation of α-aminobenzylphosphonic derivatives, which was shown using 1,3-diphenylnaphthoxazine as an example. Major diastereomers of α-aminobenzyl- and α-aminoalkylphosphonic acid derivatives of Betti base obtained according to this procedure have different relative configurations of their chiral centers.
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References
Aminophosphonic and aminophosphinic acids, Eds V. P. Kukhar, H. R. Hudson, John Wiley & Sons, New York, 2000, 634 pp.
P. Kafarski, B. Lejczak, Phosphorus, Sulfur, Silicon Relat. Elem., 1991, 63, 193.
K. E. Metlushka, B. A. Kashemirov, V. F. Zheltukhin, D. N. Sadkova, B. Büchner, C. Hess, O. N. Kataeva, Ch. E. McKenna, V. A. Alfonsov, Chem. Eur. J., 2009, 15, 6718.
C. Cardellicchio, G. Ciccarella, F. Naso, E. Schingaro, F. Scordari, Tetrahedron Asymmetry, 1998, 9, 3667
Y. Dong, R. Li, J. Lu, X. Xu, X. Wang, Y. Hu, J. Org. Chem., 2005, 70, 8617
V. A. Alfonsov, K. E. Metlushka, Ch. E. McKenna, B. A. Kashemirov, O. N. Kataeva, V. F. Zheltukhin, D. N. Sadkova, A. B. Dobrynin, Synlett, 2007, 488
G. Bian, S. Yang, H. Huang, L. Song, Synthesis, 2013, 45, 899.
H. E. Smith, N. E. Cooper, J. Org. Chem., 1970, 35, 2212.
I. Szatmári, T. A. Martinek, L. Lázár, F. Fülöp, Tetrahedron, 2003, 59, 2877.
I. Szatmári, T. A. Martinek, L. Lázár, A. Koch, E. Kleinpeter, K. Neuvonen, F. Fülöp, J. Org. Chem., 2004, 69, 3645.
D. A. Evans, K. M. Hurst, L. K. Truesdale, J. M. Takacs, Tetrahedron Lett., 1977, 2495.
V. F. Zheltukhin, K. E. Metlushka, D. N. Sadkova, Ch. E. McKenna, B. A. Kashemirov, V. A. Alfonsov, Mendeleev Commun., 2007, 17, 239.
Bruker, APEX2 Software Suite for Crystallographic Programs, Bruker AXS, Inc., Madison, Wisconsin, USA, 2009.
Bruker, Area detector control and integration software, Version 5.x, in SMART and SAINT, Madison, Wisconsin (USA): Bruker Analytical X-ray Instruments Inc., 1996.
G. M. Sheldrick, SHELX-97, Programs for Crystal Structure Analysis, University of Göttingen, Institut für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1997.
G. M. Sheldrick, Acta Crystallogr., Sect. A, 2008, A64, 112.
L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837.
L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Crystallogr., 2008, 41, 466.
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Dedicated to Academician of the Russian Academy of Sciences O. N. Chupakhin on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1390–1394, June, 2014.
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Metlushka, K.E., Sadkova, D.N., Shaimardanova, L.N. et al. Diastereoselective synthesis of α-aminoalkylphosphonic acid derivatives of Betti base. Russ Chem Bull 63, 1390–1394 (2014). https://doi.org/10.1007/s11172-014-0608-5
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DOI: https://doi.org/10.1007/s11172-014-0608-5