A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides

CORC > 北京大学 > 化学与分子工程学院

	A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides
	Cheng H ; Gan L ; Shi Y ; Wei X
刊名	the journal of organic chemistry
	2001
英文摘要	Sensitized photolysis of iminodiacetic acid methyl ester and maleimides follows a [2 + 3] cycloaddition pathway yielding pyrrolidine derivatives. This is similar to the photochemical reaction between C(60) and amines. A series of pyrrolidine derivatives are prepared by the method including multipyrrolidines from bis- and tris-maleimide starting materials. The yields range from 13% to 85%. The reaction is highly stereoselective. All the isolated products have the 1,3-dimethoxycarbonyl groups in the cis configuration. Various sensitizers may be used with slightly different yields. A plausible mechanism is proposed that involves the singlet oxygen abstraction of two alpha hydrogen atoms from the iminodiacetate and formation of a 1,3-dipole with a structure similar to the classical thermally generated 1,3-dipole.; SCI(E); EI; PubMed; 0; 19; 6369-74; 66
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/347437]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Cheng H,Gan L,Shi Y,et al. A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides[J]. the journal of organic chemistry,2001.
APA	Cheng H,Gan L,Shi Y,&Wei X.(2001).A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides.the journal of organic chemistry.
MLA	Cheng H,et al."A novel[2 + 3]cycloaddition reaction: singlet oxygen mediated formation of 1,3-dipole from iminodiacetic acid dimethyl ester and its addition to maleimides".the journal of organic chemistry (2001).