Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination

Anita E. Mattson, Andrea M. Zuhl, Troy E. Reynolds, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

129 Scopus citations

Abstract

The direct nucleophilic acylation of nitroalkenes is reported utilizing a fluoride-initiated rearrangement of protected thiazolium carbinols. The key combination of fluoride anion and thiourea accesses carbonyl anion reactivity without the use of amine or amide bases typically employed in the generation of these Umpolung nucleophiles. The mild reaction conditions used to generate the reactive carbonyl anion species in situ allow for conjugate additions in good yield to sensitive nitroalkene electrophiles. The process is tolerant of a variety of thiazolium carbinols and nitroalkene substrates and can be rendered enantioselective and diastereoselective by the addition of a chiral thiourea derived from quinine.

Original languageEnglish (US)
Pages (from-to)4932-4933
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number15
DOIs
StatePublished - Apr 19 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Direct nucleophilic acylation of nitroalkenes promoted by a fluoride anion/thiourea combination'. Together they form a unique fingerprint.

  • Cite this