Isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangements of N,N-diallyl allylic ammonium ylides

Thomas H. West, Stéphanie S. M. Spoehrle, Andrew D. Smith

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)
2 Downloads (Pure)

Abstract

The isothiourea-catalysed chemo- and enantioselective [2,3]-sigmatropic rearrangement of N,N-diallyl allylic ammonium ylides is explored as a key part of a route to free functionalised α-amino esters and piperidines. The [2,3]-sigmatropic rearrangement proceeds with excellent diastereo- and enantiocontrol (>95:5 dr, up to 97% ee), with the resultant N,N-diallyl α-amino esters undergoing either mono- or bis-N-allyl deprotection. Bis-N-allyl deprotection leads to free α-amino esters, while the mono-deprotection strategy has been utilized in the synthesis of a target functionalised piperidine.
Original languageEnglish
Pages (from-to)4138-4149
Number of pages12
JournalTetrahedron
Volume73
Issue number29
Early online date30 Jan 2017
DOIs
Publication statusPublished - 20 Jul 2017

Keywords

  • [2,3]-rearrangement
  • Isothiourea catalysis
  • Allylic ammonium ylides
  • Enantioselective catalysis
  • α-amino esters

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