Enantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalyst

Bo Zhu, Richmond Lee, Yanli Yin, Fuyuan Li, Michelle L. Coote, Zhiyong Jiang

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

An enantioselective vinylogous amination of 5-alkyl-4-nitroisoxazoles is reported. With a novel chiral dipeptide-based urea-amide-guanidinium as the phase-transfer catalyst, the reactions worked efficiently with NaOAc as the base, affording valuable and challenging-to-synthesize chiral isoxazole derivatives featuring a single stereocenter at the α-position in high yields and with excellent enantioselectivities. Theoretical studies with DFT predicted that cooperative multiple hydrogen-bonding and ion pairing interactions of a nucleophile and NaOAc with the catalyst is crucial to deprotonation by reducing their HOMO-LUMO energy gap.

Original languageEnglish
Pages (from-to)429-432
Number of pages4
JournalOrganic Letters
Volume20
Issue number2
DOIs
Publication statusPublished - 19 Jan 2018
Externally publishedYes

Keywords

  • Catalysts
  • Guanidine
  • Organic compounds
  • Organic reactions
  • Stereoselectivity

Fingerprint

Dive into the research topics of 'Enantioselective Vinylogous Amination of 5-Alkyl-4-nitroisoxazoles with a Dipeptide-Based Guanidinium Phase-Transfer Catalyst'. Together they form a unique fingerprint.

Cite this