Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Chemical Society of Japan Award for Creative Work for 2005
Development of Chiral Spiro Ligands for Metal-Catalyzed Asymmetric Reactions
Gan B. BajracharyaMidori A. AraiPriti S. KoranneTakeyuki SuzukiShinobu TakizawaHiroaki Sasai
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2009 Volume 82 Issue 3 Pages 285-302

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Abstract

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.

We have developed a range of novel chiral spiro ligands bearing N-heterocycles as metal-coordinating units. The metal complexes of these ligands displayed unprecedented activation of olefins that allowed us to develop several asymmetric transformations. Fullsize Image
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© 2009 The Chemical Society of Japan
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