Anionic Amino-Cope Rearrangement Cascade Synthesis of 2,4-Substituted Benzoate Esters from Acyclic Building Blocks

M. Haziq Qureshi, Jon T. Njardarson

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

We report a new anionic cascade for assembling 2,4-substituted benzoate esters in one pot from racemic β-fluoro-substituted conjugated tert-butylsulfinyl imines and 3-substituted methyl 2-butenoates. Dienolate formation triggers a Mannich addition followed by an amino-Cope like rearrangement, which results in immediate elimination of fluoride by a lithiated enamine. The newly formed 1,4-diene intermediate contains a highly acidic proton which is spontaneously deprotonated, leading to a facile intramolecular cyclization followed by sulfinamide group elimination and aromatization.

Original languageEnglish (US)
Pages (from-to)7978-7982
Number of pages5
JournalOrganic Letters
Volume24
Issue number43
DOIs
StatePublished - Nov 4 2022

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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