The Knoevenagel/michael Cascade Reaction And The Diastereoselectivity By Three Components Condensation With The Participation Of Phosphonate

The progress of one-pot synthesis of phosphonates and phosphates derivatives via utilizing the lone pairs of electrons in phosphorus atom to build the phosphorus-carbon bonds in Knoevenagel/Michael cascade reaction and the diastereoselectivity are comprehensively reviewed in this paper. Since one-pot reaction in which three or more reactants are combined to form a new preferred compound with high efficiency, atomic high utilization, less economical and easy to operate is known as multi-component reactions(MCRs). In this study, this method will be used to the synthesis of phosphonate by phospha-Michael addition reaction. During the study, not only be a series of new phosphonate compounds(P-Betti base) prepared, but also synthesis and separation of a couple of diastrereoisomers will be accomplished via the construction of P-C bond between L-(-)-menthyl(Rp)-phenylphosphinate with excellent spatial structure and 2-amino-4H–chromenes which has good biological pharmacological activity. As a result, this article will obtain some new compounds while pharmaceutical chemistry about phosphorus will be promoted.1?Straightforward and one-pot strategy to synthesize the ?-diarylation of benzyl phosphine oxides(P-Betti base) under solvent–free and high temperature 180 ?via the condensation of ?-naphthol, aryl aldehydes and the diphenylphosphine oxide was effectively catalyzed by p-toluenesulfonic acid in good yield(60% ~ 95%).The product structures were characterized by 1H NMR, 13 C NMR, 31 P NMR and IR. The effect of different reaction conditions on yield and the proposed mechanism of the cascade reaction had been investigated.2?At room temprature the condention between salicylaldehyde, malononitrile and(-)-menthyl-(RP)-benzylphosphinate for the preparation of(11Sp,8Rc)-(2-amino-3-cyano-4H-chromene-4-yl) menthyl benzylphosphinate has been developed in ethanol in the presence of aluminium chloride. The products' structures were characterized by IR, 1H NMR, 13 C NMR, 31 P NMR and elemental analysis. The effect of different reaction conditions on yield and the proposed mechanism of the cascade reaction had been investigated.3?In order to further confirm the absolute configuration of the isolated product 3n and Sp-Rc, the compounds 3n and Sp-Rc were recrystallized, obtained as stable, white crystals and determined by X-ray diffraction analysis. 3n is proved to be consisted of a couple of racemic modifications. While Sp-Rc is proved to be a pure compound with a chiral carbon and a chiral phosphorus(11Sp,8Rc) by its absolute configuration.