Regiospecific and Highly Stereoselective Synthesis of β-Amino(E)-Enylphosphonates via β-Hydrogen Mig

• 作 者: HaihongGe;YanCai;ZhiweiMiao;
• 机 构: State Key Laboratory and Institute of Elemento-organic Chemistry,Collaborative Innovation Center of
• 出 处: 中国化学会第29届学术年会
• 发表日期: 2014年期

　　Carbenoid chemistry has become a powerful tool in organic synthesis,diazo compounds are commonly used important precursors of metal carbene,and they have attracted considerable attentions over the past decades due to their diverse reactivities1.In contrast to that found in α-diazo carbonyl compounds,α-diazophosphonyl compounds have not been studied systematically in metal carbene reactions.Recently,we reported that tertiary β-alkoxy substituted β-amino phosphonates derivatives could be synthesized by treatment of α-diazophosphonyl compounds,which derived from natural amino acids,with alcohols catalyzed by copper(Ⅰ) salts at room temperature.company with the(Z)-β-enaminophosphonates formed as the 1,2-hydrogen migration product,in the absent of alcohols,an unexpected β,γ-dihydrogen shift reaction was also discovered.Therefore,continuing with our interest in the chemistry of these novel α-diazophosphonyl compounds2,here we reported our recent investigations on the reaction between these α-diazophosphonyl compounds under the catalysis of [Cu(MeCN)4]PF6 to synthesize β-amino(E)-enylphosphonates derivatives with DMF as additive(Scheme 1).