Efficient synthesis of 1,3,5-trisubstituted (pyrrol-2-yl)acetic acid esters via dual nucleophilic reactions of sulfonamides or carbamate with 4-trimethyl-siloxy-(5E)-hexen-2-ynoates: Lewis acid catalyzed SN1 and intramolecular Michael addition

Teruhiko Ishikawa, Toshiaki Aikawa, Shinichiro Watanabe, Seiki Saito

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Carbamates or sulfonamides have proven to regioselectively attack 2-propynyl-allyl hybrid cations, generated by the action of TMSOTf on 4-(trimethylsioxy)hex-5-en-2-ynoates, to afford conjugated 6-aminohex-4-en-2- ynoates in which an intramolecular amino-Michael reaction took place, leading to pyrrole frameworks. In particular, the sulfonamides gave 1-sulfonylpyrroles in one pot.

Original languageEnglish
Pages (from-to)3881-3884
Number of pages4
JournalOrganic Letters
Volume8
Issue number17
DOIs
Publication statusPublished - Aug 17 2006

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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