The copper-catalyzed asymmetric construction of a dispiropyrrolidine skeleton via 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides

Research output: Contribution to journalArticle

Authors

  • Wu-Lin Yang
  • Yang-Zi Liu
  • Shuai Luo
  • Xingxin Yu
  • Wei-Ping Deng

Colleges, School and Institutes

External organisations

  • Shanghai Key Laboratory of New Drug Design & School of Pharmacy, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.

Abstract

A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to α-alkylidene succinimides catalyzed by a novel chiral N,O-ligand/Cu(OAc)2 system is reported, affording dispiropyrrolidine derivatives with spiro quaternary stereogenic centers in good to excellent yields (up to 90%), excellent levels of diastereoselectivities (>20 : 1 dr) and enantioselectivities (up to 97% ee).

Details

Original languageEnglish
Pages (from-to)9212-9215
Number of pages4
JournalChemical Communications
Volume51
Issue number44
Early online date28 Apr 2015
Publication statusPublished - 19 May 2015