Rh(â…¡)-catalyzed Mannich-Type And Aldol-Type Multi-component Reaction Based On Trapping Of Water Hydroxyl Oxnium Ylides

Herein we introduce two new multi-component reactions intermediated by water hydroxyl oxnium ylide, approachs to P-phenyl isoserines and a,β-dihydroxyl esters.In this thesis, the reactions former-mentioned will be elaborated mainly in two aspects:1) the detailed investigation of Mannich-type reaction 2) the primary study on aldol-type reaction.In the first part, the research of Mannich-type reaction is divided into three stages. In the first one, the chemo- and diastereoselectivity of the reaction is investigated. In the second one, upon the base of in-situ generation of diazo by oxidation of amino acid, a one pot process is developed for the the Mannich-type reaction. In the last stage, research of asymmetric catalysis of the reaction is depicted.Firstly, we disclose a muti-component reaction of ethyl diazoacetate (EDA), water and N-phenylbenzaldimine, which characterizes with good component match of water and high diastereoselectivity in imine substrates with electron-withdraw groups. The reaction offeres a new process for the synthesis ofβ-phenyl isoserine derivatives and uncovers the significance of component match in MCRs. The improved one-pot process simplifies the procedure of synthesis of isoserine derivatives and extends the scope of substrates to a-alkyldiazoesters.Secondly, we investigate the stereoselectivity of the reaction by using ethyl methyldiazoacetate, water and N-(4-methoxy-Phenyl)-benzaldimine as starting materials. Eventually, we establishe chiral phorsphoric acid, toluene, L-tartaric acid as the fit catalyst, solvent and additive respectively. Ideal results could be gained in the process of extending substrates.(ee.up to 95%, yield up to 80%, dr.up to 3:1). The highly enatioselective reaction is an unprecedented protocol which transforms the readily avaliable materials to enatiopure isoserine derivatives in a concise way.In the second part, the primary study of aldol-type reaction is discussed, which intends to pave the way for the asymmetric catalysis of the reaction.