School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, People's Republic of China.
J Org Chem. 2017 Oct 20;82(20):11141-11149. doi: 10.1021/acs.joc.7b02142. Epub 2017 Oct 4.
A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to β,β-disubstituted β-fluoroacrylates catalyzed by a chiral N,O-ligand/Cu(CHCN)BF system is reported, affording chiral densely substituted pyrrolidines with four contiguous stereocenters, including one fluorinated quaternary stereocenter at the 3-position, in good to excellent yields (up to 99%), with excellent levels of diastereo- and enantioselectivities (dr >20:1; ee up to 99%).
报道了一种手性 N,O-配体/Cu(CHCN)BF 体系催化的亚胺叶立德与β,β-二取代β-氟代丙烯酸酯的高效不对称 1,3-偶极环加成反应，以良好至优异的收率（高达 99%），获得了具有四个连续立体中心的手性稠环取代吡咯烷，包括 3-位的氟代季碳立体中心，对映选择性和非对映选择性极好（dr>20:1；ee 高达 99%）。
