title: Highly Stereoselective [3+2] Cycloadditions of Chiral Palladium-Containing N(1) -1,3-Dipoles: A Divergent Approach to Enantioenriched Spirooxindoles.
abstract: A catalytic asymmetric [3+2] cycloaddition reaction of chiral palladium-containing N(1) -1,3-dipoles with methyleneindolinones has been successfully developed. The reaction allows an efficient construction of 3,3'-pyrrolinyl spirooxindoles with high yields and excellent stereoselectivities (up to 93 % yield, 19:1 d.r. and >99 % ee). A synthetic application of this methodology is demonstrated and a stereocontrol mechanism is proposed.
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China.
authors.forename: Tian-Ren
authors.initials: TR
authors.lastname: Li
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China.
authors.forename: Bei-Yi
authors.initials: BY
authors.lastname: Cheng
authors.affiliation: Department of Chemistry, University of Oregon, 1585 E 13th Ave., Eugene, OR, 97403, USA.
authors.forename: Si-Qi
authors.initials: SQ
authors.lastname: Fan
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China.
authors.forename: Ya-Ni
authors.initials: YN
authors.lastname: Wang
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China. luliangqiu@mail.ccnu.edu.cn.
authors.forename: Liang-Qiu
authors.initials: LQ
authors.lastname: Lu
authors.affiliation: CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticides and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, P. R. China.|Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin, 300072, P. R. China.
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Xiao
keywords: asymmetric catalysis; aziridines; organic chemistry; palladium; spirooxindole