Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

A range of pyrazolidin-3-ones have been prepared and their activity as catalysts for iminium-ion promoted Diels-Alder reactions evaluated. Systematic variation of the C(5)- and N(2)-substituents indicates that the incorporation of an electron withdrawing substitutent at N(2) and either a Ph or CF3 substitution at C(5) results in optimal catalytic activity. The diastereoisomeric resolution of a model C(5)-Ph substituted pyrazolidinone and its ability to impart modest levels of asymmetric induction in the organocatalytic Diels-Alder reaction is also demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)8992-9008
Number of pages17
JournalTetrahedron
Volume66
Issue number46
DOIs
Publication statusPublished - 13 Nov 2010

Keywords

  • IMINIUM ION CATALYSIS
  • C-CARBOXYL TRANSFER
  • ORGANIC CATALYSIS
  • AZOMETHINE IMINES
  • O-CARBOXYL
  • ACCELERATION
  • DERIVATIVES
  • STRATEGIES
  • CARBONATES
  • HYDRAZINES

Fingerprint

Dive into the research topics of 'Structural effects in pyrazolidinone-mediated organocatalytic Diels-Alder reactions'. Together they form a unique fingerprint.

Cite this