Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita-Baylis-Hillman-type reaction

James E. Kitulagoda, Anders Palmelund, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

Abstract

An aza-Morita-Baylis-Hillman-type reaction of Michael acceptors with 5-substituted cyclic N,O-acetals derived from pyrrolidines has been investigated. It has been found that the combination of Me(2)S and TMSOTf work well with unhindered and reactive enals and enones whilst the use of quinuclidine and TMSOTf is superior for more hindered Michael acceptors. The reactions lead to 2,5-trans-disubstituted pyrrolidines with good to excellent diastereoselectivity. The origin of the selectivity is discussed. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)6293-6299
Number of pages7
JournalTetrahedron
Volume66
Issue number33
DOIs
Publication statusPublished - 14 Aug 2010
Event10th Tetrahedron Symposium on Challenges in Organic and Bioorganic Chemistry - Paris, France
Duration: 23 Jun 200926 Jun 2009

Keywords

  • N-ACYLIMINIUM IONS
  • D-RING FRAGMENTS
  • TRANS-2,5-DISUBSTITUTED PYRROLIDINES
  • ASYMMETRIC INDUCTION
  • CHIRAL AUXILIARIES
  • ENANTIOSELECTIVE SYNTHESIS
  • ELECTROCHEMICAL OXIDATION
  • STEREOSELECTIVE ADDITION
  • CLAISEN REARRANGEMENTS
  • ORGANOCOPPER REAGENTS

Cite this