Synthesis Of Chiral Ammonium Betaine And Addition Reaction Of Diphenylphosphino To The Aldehyde

The thesis is divided into two parts, the first is focused on the studies of the chiralcatalysts of betaine ammonium salts and chiral phosphoric acid catalysts for theirsynthesis as well as catalytic asymmetric Mannich reaction; the second part describes thediversity reactions between the salicylaldehyde and diphenyl phosphine chloride.With the rapid progress for asymmetric synthesis methods in recent years, smallorganic molecule catalytic reaction has attracted more interest of the organic chemists forits mild reaction conditions, no metal, low toxicity, atom economy and similar enzymaticcharacteristics and so on. In this paper, a series of chiral catalysts of betaine ammoniumsalts are designed using L-phenylalanine, L-valine and L-proline as starting materials.The results show that if the cyclic tertiary amines with larger steric hindrance, alkylationof tertiary amines can not be achieved and so do the betaine ammonium salt.In addition, we have synthesized a new chiral phosphoric acid catalyst, using the[1-((S)-pheny(((1'S)-1'-phenylethyl)amino)-methyl)-2-naphthol] as the starting material,which show certain activity in catalytic asymmetric Mannich reaction, and which alsoshould be further optimized the structure of chiral phosphoric acid to improve thereactivity and selectivity of the asymmetric catalytic reaction.Diphenyl phosphine chloride (Ph2PCl), one of the most important ligands for thesynthesis of various organophorus compounds, is an important chemical intermediate,which can be transferred to a number of chemical products. In the synthesis of2-(diphenylphosphinooxy) benzaldehyde using the salicylaldehyde and diphenylphosphine chloride as starting materials, a new type of organic phosphonate compoundswith intense fluorescence were obtained unexpectedly. During optimizing the reactionconditions, different types of organic phosphine compounds can be prepared by changingthe solvent and /or base. The variability and complexity of the organic phosphinechemistry were verified again.In this paper, all the new organic phosphine compounds are characterized andconfirmed by the 1H and 13C NMR, 31P NMR and X-ray diffraction, etc. This study hasdeveloped an efficient synthetic method of amino acid derivatives, and a reasonablereaction mechanism was supposed and discussed.