5-Substituted 3-(diethoxyphosphoryl)isoxazoles and -2- isoxazolines were synthesized regioselectively by 1,3-dipolar cy- cloaddition of (diethoxyphosphoryl)formonitrile oxide to monosub- stituted alkynes and alkenes. By applying this methodology to an N- (tert-butoxycarbonyl)-substituted allylglycine methyl ester, we prepared the precursors of two diastereomeric 3-phosphono-2-isoxazo- lin-5-yl-substituted amino acids, which are bioisosteres of potent NMDA receptor antagonists.
A regioselective route to 5-substituted isoxazoline-3-phosphonates / P. Conti, A. Pinto, L. Tamborini, P. Dunkel, V. Gambaro, G.L. Visconti, C. De Micheli. - In: SYNTHESIS. - ISSN 0039-7881. - 2009:4(2009 Feb 16), pp. 591-596. [10.1055/s-0028-1083343]
A regioselective route to 5-substituted isoxazoline-3-phosphonates
P. Conti
Primo
;A. PintoSecondo
;L. Tamborini;V. Gambaro;G.L. ViscontiPenultimo
;C. De MicheliUltimo
2009
Abstract
5-Substituted 3-(diethoxyphosphoryl)isoxazoles and -2- isoxazolines were synthesized regioselectively by 1,3-dipolar cy- cloaddition of (diethoxyphosphoryl)formonitrile oxide to monosub- stituted alkynes and alkenes. By applying this methodology to an N- (tert-butoxycarbonyl)-substituted allylglycine methyl ester, we prepared the precursors of two diastereomeric 3-phosphono-2-isoxazo- lin-5-yl-substituted amino acids, which are bioisosteres of potent NMDA receptor antagonists.
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