Development of Chiral Spiro Ligands for Metal-Catalyzed Asymmetric Reactions

This account focuses our works on the development of chiral spiro ligands bearing N-heterocycles as metal-coordinating units and their applications in the metal-catalyzed asymmetric reactions. The spiro bis(isoxazoline) ligands (SPRIXs), spiro bis(isoxazole) ligands, and spiro (isoxazole–isoxazoline...

Full description

Saved in:
Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2009-03, Vol.82 (3), p.285-302
Main Authors: Bajracharya, Gan B, Arai, Midori A, Koranne, Priti S, Suzuki, Takeyuki, Takizawa, Shinobu, Sasai, Hiroaki
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:This account focuses our works on the development of chiral spiro ligands bearing N-heterocycles as metal-coordinating 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 PdII 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 enantioselective version of the aminocarbonylation proceeded for the first time. Other hitherto known chiral ligands we examined failed to promote these reactions.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.82.285