- Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings
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Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P-H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation, by Michael addition or by P-arylation. These reactions present generally a good or even an excellent kinetic diastereoselectivity which can often be predicted by molecular models of the transition states.
- Cristau, Henri-Jean,Pirat, Jean-Luc,Virieux, David,Monbrun, Jér?me,Ciptadi, Ciptadi,Bekro, Yves-Alain
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p. 2472 - 2481
(2007/10/03)
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- METALLATION OF BENZYLIDENEBENZYLAMINE
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The reactions of benzylidenebenzylamine with methyllithium and lithium diethylamide were investigated by GLC.Products with different structures from condensation of the azomethine are formed: Cyclic 2,4,5-triphenyl-3-benzylimidazolidine and noncyclic dibenzylidene-1,2-diphenylethylenediamine.Investigation of the effects of the solvent, temperature, and ratio of reagents on the reaction made it possible to obtain conditions for synthetic application of the 1,3-diphenylazaallyllithium, obtained by metallation of benzylidenebenzylamine, in reactions with alkyl halides, carbon dioxide, carbonyl compounds, and phenyl isocyanate.These conditions involve a temperature between -60 and -70 deg C and an equimolar ratio between the reagents.
- Gracheva, R. A.,Potapov, V. M.,Sivov, N. A.,Sivova, L. I.
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p. 1963 - 1970
(2007/10/02)
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