Diastereoselective [2,3]-Sigmatropic Rearrangement of N-Allyl Ammonium Ylides

Aleksandra Murre, Kristin Erkman, Sandra Kaabel, Ivar Järving, Tõnis Kanger*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

3 Citations (Scopus)

Abstract

A rapid and diastereoselective method was developed for the [2,3]-sigmatropic rearrangement of N-Allyl ammonium ylides, affording products in up to 95% isolated yields and up to 97:3 dr; most of the desired products were formed within 1 minute. For the asymmetric reaction, a chiral auxiliary was introduced to the starting compound, affording the rearrangement product with high diastereoselectivities.

Original languageEnglish
Pages (from-to)4183-4197
Number of pages15
JournalSynthesis (Germany)
Volume51
Issue number22
DOIs
Publication statusPublished - 2019
MoE publication typeA1 Journal article-refereed

Keywords

  • ammonium ylide
  • auxiliary
  • diastereoselectivity
  • oxazolidinyl group
  • [2,3]-sigmatropic rearrangement
  • α-Amino ketones

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