title: exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(I)/DTBM-BIPHEP.
abstract: An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China. cjwang@whu.edu.cn.
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Li
authors.forename: Tang-Lin
authors.initials: TL
authors.lastname: Liu
authors.forename: Liang
authors.initials: L
authors.lastname: Wei
authors.forename: Xiang
authors.initials: X
authors.lastname: Zhou
authors.forename: Hai-Yan
authors.initials: HY
authors.lastname: Tao
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D001713:Biphenyl Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D061565:Cycloaddition Reaction; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: C437189:2,2'-bis(diphenylphosphino)-1,1'-biphenyl; D001391:Azo Compounds; D001713:Biphenyl Compounds; D011759:Pyrrolidines; D013141:Spiro Compounds; D013882:Thiosemicarbazones; C512188:azomethine; C014096:alpha-methylene gamma-butyrolactone; D003300:Copper; C032519:pyrrolidine; D015107:4-Butyrolactone