【摘 要】
：
The 1,3-dipolar cycloaddition reaction of azomethine ylides with alkenes is one of the most extensively studied organic reactions.Traditionally,the azomethine ylide was usually generated from the cond
【机 构】
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College of Chemistry & Chemical Engineering,Yangzhou University,Yangzhou 225002
【出 处】
：
中国化学会全国第十二届有机合成化学学术研讨会
论文部分内容阅读
The 1,3-dipolar cycloaddition reaction of azomethine ylides with alkenes is one of the most extensively studied organic reactions.Traditionally,the azomethine ylide was usually generated from the condensation of an amine with an aldehyde,followed by deprotonation of the iminium ion or prototropic shift of the imine.We envisioned that a new type azomethine ylide could be generated by the reaction of amino acid with electron-deficient alkynes.The three-component reaction of secondary α-amino acids including proline,sarcosine,thiazolidine-4-carboxylic acid with dialkyl acetylenedicarboxylate and 3-methyleneoxindoles in refluxing ethanol afforded functionalized spiro[indoline-3,2-pyrrolizines],spiro[indoline-3,3-pyrrolidines] and spiro[indoline-3,6-pyrrolo[1,2-c]thiazoles] in good yields and with high diastereoselectivity.Furthermore,the similar multicomponent reactions containing primary α-amino acids such as glycine,alanine and phenylalanine resulted in the corresponidng(spiro[indoline-3,3-pyrrolidine]-1-yl)maleates.
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