Stereoselective addition of sulfone carbanions to C=N: A critical dependence on the stability and reactivity of the amide anions in MIRC reactions

Alfred Hassner, Diana Usak, Ramaiah Kumareswaran, Oded Friedman

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A procedure was developed for the selective synthesis of functionalized 4-methylenepyrrolidines by tuning the electron-withdrawing group (ArSO 2, COOEt, ArSO) attached to the acceptor imine nitrogen atom during addition of allyl sulfone carbanions. Sulfone carbanion additions to 2H-azirines were also examined.

Original languageEnglish
Pages (from-to)2421-2426
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number11
DOIs
StatePublished - 24 May 2004

Keywords

  • Cyclization
  • Diastereoselectivity
  • Imines
  • Pyrrolidines

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