Telescoped Synthesis of Stereodefined Pyrrolidines

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Abstract

Telescoped and one-pot olefination/asymmetric functionalization approaches to disubstituted pyrrolidines (dr up to 99:1, up to 99% ee) have been developed using commercially available tetramisole (0.1 to 5 mol %). Using OTMS-quinidine as the Lewis base gives preferential access to an anti-configured pyrrolidine in high enantioselectivity.

Original languageEnglish
Pages (from-to)3472-3475
Number of pages4
JournalOrganic Letters
Volume15
Issue number13
Early online date25 Jun 2013
DOIs
Publication statusPublished - 2013

Keywords

  • CATALYZED ALDOL-LACTONIZATION
  • TRICYCLIC BETA-LACTONES
  • ASYMMETRIC-SYNTHESIS
  • KINETIC RESOLUTION
  • CONJUGATE ADDITION
  • ACID
  • BENZOTETRAMISOLE
  • ORGANOCATALYSIS
  • CYCLOADDITION
  • ALKALOIDS

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