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

doi:10.1021/jo015749m

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, LB ; Shi, YR ; Wei, XL
刊名	journal of organic chemistry
	2001
关键词	ELECTRON-TRANSFER REACTIONS PYRROLIDINE DERIVATIVES AZOMETHINE YLIDES < FULLERENE < TRIETHYLAMINE AMINES C-60 60> 2+3> FULLERENE -CYCLOADDITION
DOI	10.1021/jo015749m
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.; Chemistry, Organic; SCI(E); EI; 19; 19; 6369-6374; 66
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/258069]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Cheng, H,Gan, LB,Shi, YR,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]. journal of organic chemistry,2001.
APA	Cheng, H,Gan, LB,Shi, YR,&Wei, XL.(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.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".journal of organic chemistry (2001).