Abstract
Phosphorylacetic acid esters containing the menthoxy fragment at the phosphorus atom or at the carbonyl group were synthesized. The configurations of the enantiomerically pure compounds, viz., methyl (ethoxy)(menthyloxy)phosphorylacetate and menthyl [(2-chloro-ethoxy)(4-dimethylaminophenyl)phosphoryl]acetate, were established by X-ray diffraction and NMR spectroscopy.
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V. P. Kukhar’, N. Yu. Svistunova, V. A. Solodenko, and V. A. Soloshonok, Usp. Khim., 1993, 62, 284 [Russ. Chem. Rev., 1993, 62 (Engl. Transl.)].
R. I. Tarasova and V. V. Moskva, Zh. Obshch. Khim., 1997, 67, 1483 [Russ. J. Gen. Chem., 1997, 67 (Engl. Transl.)].
I. Semina, E. Shilovskaya, R. Tarasova, A. Baichurina, V. Pavlov, N. Tikhonova, and R. Garaev, Phosphorus, Sulfur, and Silicon, 1990, 144–145, 753.
I. I. Semina, E. V. Shilovskaya, R. I. Tarasova, A. Z. Baichurina, V. A. Pavlov, N. A. Tikhonova, I. Kh. Valeeva, and R. S. Garaev, Khim.-farm. Zh., 2002, 35, Issue 4, 3 [Pharm. Chem. J., 2002, 35, Issue 4 (Engl. Transl.)].
R. I. Tarasova, O. V. Voskresenskaya, R. M. Eliseenkova, I. I. Semina, E. V. Shilovskaya, Sh. K. Latypov, A. A. Balandina, and A. A. Bredikhin, Khim.-farm. Zh., 2006, 40, Issue 9, 9 [Pharm. Chem. J., 2006, 40, Issue 9 (Engl. Transl.)].
R. I. Tarasova, O. V. Voskresenskaya, K. V. Pinyagin, V. V. Moskva, A. V. Litvinenko, A. V. Khudenko, M. A. Shchelkunova, V. G. Nikolaeva, G. A. Mandrov, and I. T. Boikov, Zh. Prikl. Khim., 1990, 63, 878 [J. Appl. Chem. USSR, 1990, 63 (Engl. Transl.)].
R. A. Lewis, O. Korpiun, and R. Mislow, J. Am. Chem. Soc., 1968, 90, 4847.
H. Günther, NMR Spectroscopy, An Introduction, J. Wiley and Sons, Chichester—New York—Brisbane—Toronto, 1980.
O. I. Kolodiazhnyi, I. V. Guliaiko, and A. O. Kolodiazhna, Tetrahedron Lett., 2004, 45, 6955.
A. E. Derome, Modern NMR Techniques for Chemistry Research, Pergamon, Oxford, 1988; Atta-ur-Rahman, One and Two Dimensional NMR Spectroscopy, Elsevier, Amsterdam, 1989, 579; T. Parella, Magn. Reson. Chem., 1998, 36, 467; M. Findeisen and S. Berger, Magn. Reson. Chem., 2003, 41, 431; R. Crouch, R. D. Boyer, R. Johnson, and K. Krishnamurthy, Magn. Reson. Chem., 2004, 42, 301; T. Sprang and P. Bigler, Magn. Reson. Chem., 2004, 42, 55.
K. Stott, J. Stonehouse, J. Keeler, T. L. Hwang, and A. J. Shaka, J. Am. Chem. Soc., 1995, 117, 4199.
Sh. K. Latypov, J. M. Seco, E. Quiñoá, and R. Riguera, J. Org. Chem., 1995, 60, 504; Sh. K. Latypov, A. V. Aganov, S. Tahara, and Y. Fukushi, Tetrahedron, 1999, 55, 7305; M. J. Ferreiro, Sh. K. Latypov, E. Quiñoá, and R. Riguera, J. Org. Chem., 2000, 65, 2658.
N. L. Allinger, J. Am. Chem. Soc., 1977, 99, 8127; N. L. Allinger, R. A. Kok, and M. R. Imam, J. Comput. Chem., 1988, 9, 591; J.-H. Lii, S. Gallion, C. Bender, H. Wikstrom, N. L. Allinger, K. M. Flurchick, and M. M. Teeter, J. Comput. Chem., 1989, 10, 503.
A. Altomare, G. Cascarano, C. Giacovazzo, and D. Viterbo, Acta Crystallogr., Sect. A, 1991, 47, 744.
L. H. Straver and A. J. Schierbeek, MolEN. Structure Determination System. Vol. 1. Program Description, B.V. Nonius, 1994, 180.
A. L. Spek, Acta Crystallogr., Sect. A, 1990, 46, 34.
W. C. Hamilton, Acta Crystallogr., 1965, 18, 502.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 281–288, February, 2007.
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Bredikhin, A.A., Eliseenkova, R.M., Tarasova, R.I. et al. Nonracemic menthyl phosphorylacetates. Russ Chem Bull 56, 290–297 (2007). https://doi.org/10.1007/s11172-007-0047-7
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DOI: https://doi.org/10.1007/s11172-007-0047-7