Development of chiral spiro ligands for metal-catalyzed asymmetric reactions

Gan B. Bajracharya, Midori A. Arai, Priti S. Koranne, Takeyuki Suzuki, Shinobu Takizawa, Hiroaki Sasai

Research output: Contribution to journalArticle

71 Citations (Scopus)

Abstract

This account focuses our works on the development of chiral spiro ligands bearing N-heterocycles as metalcoordinating units and their applications in the metal-catalyzed asymmetric reactions. The spiro bis(isoxazoline) ligands (SPRIXs), spiro bis(isoxazole) ligands, and spiro (isoxazole-isoxazoline) ligands were readily synthesized through intramolecular double nitrile oxide cycloaddition of the corresponding dioximes as a key step. An unprecedented activation of olefins was displayed by the Pd II complexes of these chiral spiro ligands in the enantioselective oxidative cyclizations, for example; the asymmetric tandem cyclization of dialkenyl alcohol via oxy-palladation produced a bicyclic ether in excellent enantioselectivity and enantio selective version of the aminocarbonylation proceeded for the first time. Other hitherto known chiral ligands we examined failed to promote these reactions.

Original languageEnglish
Pages (from-to)285-302
Number of pages18
JournalBulletin of the Chemical Society of Japan
Volume82
Issue number3
DOIs
Publication statusPublished - 2009 Apr 1
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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