Abstract
A method for obtaining of chiral phosphonobenzaldehydes has been developed. The Abramov reaction between dimenthyl phosphite and 4-diethoxymethylbenzaldehyde followed by separation of stereoisomers has yielded enantiomerically pure (1S)- and (1R)-1-hydroxyphosphonates. The resulting phosphonates, after removal of acetal protection, have been converted to (1S)- and (1R)-1-hydroxymethylphosphonobenzaldehydes. By reacting with (diethylamino)trifluorosulfurane, 1-hydroxyphosphonates have been converted to 4-(1-fluoromethyl)phosphonobenzaldehydes. The synthesized chiral phosphonobenzaldehydes are convenient chiral reactants for the preparation of phosphorus analogs of natural compounds, as has been shown with the example of synthesis of the phosphonium analog of phosphotyrosine.
Similar content being viewed by others
References
Li, P., Zhang, M., Peach, M.L., Liu, H., Yang, D., and Roller, P.P., Org. Lett., 2003, vol. 5, no. 17, p. 3095. doi 10.1021/ol035078+
Gulyaiko, I.V. and Kolodyazhnyi O.I., Russ. J. Gen. Chem., 2009, vol. 79, no. 1, p. 148. doi 10.1134/S1070363209010277
Tulsi, N.S., Downey, A.M., and Cairo, C.W., Bioorg. Med. Chem., 2010, vol. 18, no. 24, p. 8679. doi 10.1016/j.bmc.2010.09.040
Burke, T.R., Smyth, M.S., Nomizu, M., Otaka, A., and Roller, P.P., J. Org. Chem., 1993, vol. 58, no. 6, p. 1336. doi 10.1021/jo00058a009
Smith, M.S., Ford, H., Jr., and Burke, T.R., Jr., Tetrahedron Lett., 1992, vol. 33, no. 29, p. 4137. doi 10.1016/S0040-4039(00)74672-7
Kolodiazhnyi, O.I., Tetrahedron. Asymmetry, 2005, vol. 16, no. 20, p. 3295. doi 10.1016/j.tetasy.2005.09.007
Dale, J.A. and Mosher, H.S., J. Am. Chem. Soc., 1973, vol. 95, no. 2, p. 512. doi 10.1021/ja00783a034
Kolodyazhnyi, O.I., Kolodyazhnaya, A.O., and Kukhar’, V.P., Russ. J. Gen. Chem., 2006, vol. 76, no. 8, p. 1342. doi 10.1134/S1070363206080354
Knittel, D., Synthesis, 1985, no. 1, p. 186. doi 10.1055/s-1985-31149
Krause, D. and Van Etten, R., New England J. Med., 2005, vol. 353, no. 2, p. 172. doi 10.1056/NEJMra044389
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.O. Kolodyazhna, E.V. Grishkun, O.I. Kolodyazhnyi, 2017, published in Zhurnal Obshchei Khimii, 2017, Vol. 87, No. 5, pp. 801–806.
Rights and permissions
About this article
Cite this article
Kolodyazhna, A.O., Grishkun, E.V. & Kolodyazhnyi, O.I. Synthesis of chiral phosphonobenzaldehydes and phosphonotyrosine. Russ J Gen Chem 87, 991–996 (2017). https://doi.org/10.1134/S1070363217050176
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363217050176