Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes

James E. Taylor, David S. B. Daniels, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

Asymmetric alpha-amination through an N-heterocyclic carbene (NHC)-catalyzed redox reaction of alpha-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form alpha-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N-N bond cleavage.

Original languageEnglish
Pages (from-to)6058-6061
Number of pages4
JournalOrganic Letters
Volume15
Issue number23
DOIs
Publication statusPublished - 6 Dec 2013

Keywords

  • DIELS-ALDER REACTIONS
  • N-HETEROCYCLIC CARBENES
  • CARBONYL-COMPOUNDS
  • AMINO-ACIDS
  • ENANTIOSELECTIVE SYNTHESIS
  • 4+2 CYCLOADDITION
  • ARYL HALIDES
  • ALDEHYDES
  • ACTIVATION
  • ESTERS

Fingerprint

Dive into the research topics of 'Asymmetric NHC-Catalyzed Redox alpha-Amination of alpha-Aroyloxyaldehydes'. Together they form a unique fingerprint.

Cite this