Abstract
Stereochemistry of addition of di- and trialkyl phosphites to C=N compounds was investigated. Reactions of achiral dialkyl phosphites with chiral aldimines as well as that of chiral di-(1R,2S,5R)-menthyl phosphite with achiral aldimines result in low diastereomeric enrichment of the addition compound. Reaction stereoselectivity increased when supplementary chiral inductor was introduced to the reaction system. Reaction of di-(1R,2S, 5R)-menthyl phosphite with (S)-α-methylbenzylbenzaldimine proceeds as concerted asymmetric induction to form practically one diastereomer of N-substituted aminophosphonic acid. However, reaction of di-(1R,2S, 5R)-menthyl phosphite with (R)-α-methylbenzylbenzaldimine proceeded as not concerted asymmetric induction, and diastereomeric enrichment of the product was low. By chemical extrapolation, absolute configuration of compounds formed was established. Tri-(1R,2S,5R)-menthyl phosphite reacts with C=N compounds in the presence of boron trifluoride etherate to form aminophosphonic acid derivatives with the absolute configuration opposite to that appearing in the reaction of di-(1R,2S,5R)-menthyl phosphite with the same C=N compounds.
Similar content being viewed by others
REFERENCES
Kolodiazhnyi, O.I., Tetrahedron, 2003, vol. 59, no.32, p. 5923.
Kolodiazhnyi, O.I., Sheiko, S.Yu., Guliaiko, I.V., and Gryshkun, E.V., Phosphorus, Sulfur, Silicon and Relat. Elem., 2002, vol. 177, nos.8–9, p. 2269.
Kolodiazhnyi, O.I and Sheiko, S.Yu., Zh. Obshch. Khim., 2001, vol. 71, no.7, p. 977.
Kolodiazhnyi, O.I., Grishkun, E.V., Sheiko, S., Demchuk, O., Thoennessen, H., Jones, P., and Schmutzler, R., Tetrahedron: Asymmetry, 1998, vol. 9, no.10, p. 1645.
Kolodiazhnyi, O.I., Sheiko, O., and Grishkun, E.V., Heteroatom. Chem., 2000, vol. 11, no.2, p. 138.
Kolodiazhnyi, O.I., Grishkun, E.V., Sheiko, S.Yu., and Demchuk, O., Izv. Ross. Akad. Nauk, Ser. Khim., 1998, vol. 9, no.11, p. 1588.
Gilmore, W.F. and McBride, H.A., J. Am. Chem. Soc., 1972, vol. 94, no.12, p. 4361.
Blazis, V.J., Koeller, K.J., and Spilling, S.D., Tetrahedron: Asymmetry, 1994, vol. 5, no.4, p. 499.
Kafarski, P., Lejczak, B. and Szewczyk, J., Can. J. Chem., 1983, vol. 61, p. 2425.
Kolodiazhnyi, O.I., Tetrahedron: Asymmetry, 1998, vol. 9, no.8, p. 1279.
Sheiko, S.Yu., Diss. Thesis, Kiev, 2002.
Author information
Authors and Affiliations
Additional information
__________
Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 11, 2005, pp. 1818–1826.
Original Russian Text Copyright © 2005 by Kachkovskii, Andrushko, Sheiko, Kolodyazhnyi.
Rights and permissions
About this article
Cite this article
Kachkovskii, G.A., Andrushko, N.V., Sheiko, S.Y. et al. Dual Stereochemical Control in Reaction of Di- and Trialkyl Phosphites with Aldimines. Russ J Gen Chem 75, 1735–1743 (2005). https://doi.org/10.1007/s11176-005-0502-9
Received:
Issue Date:
DOI: https://doi.org/10.1007/s11176-005-0502-9