Design and synthesis of the first spiro bis(isoxazoline) derivatives as asymmetric ligands

Midori A. Arai, Takayoshi Arai, Hiroaki Sasai

Research output: Contribution to journalArticle

93 Citations (Scopus)

Abstract

(formula presented) A chiral bis(isoxazoline) ligand (SPRIX) containing a rigid spiro skeleton was designed and synthesized via a double intramolecular nitrile oxide cycloaddition. The optically pure SPRIX greatly accelerated the Cu(acac)2-catalyzed asymmetric reaction of diisopropylzinc with cyclohexenone to give the Michael adduct with 49% ee. This is the first example of the use of an isoxazoline ligand for a transition metal-catalyzed reaction. The X-ray crystallographic analysis of the hexacoordinated copper complex of SPRIX confirmed the ligand character.

Original languageEnglish
Pages (from-to)1795-1797
Number of pages3
JournalOrganic Letters
Volume1
Issue number11
DOIs
Publication statusPublished - 1999 Dec 2
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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