Development of Chiral Spiro Ligands for Metal-Catalyzed Asymmetric Reactions

被引：79

作者：

Bajracharya, Gan B. ^{[1
]}

Arai, Midori A. ^{[1
]}

Koranne, Priti S. ^{[1
]}

Suzuki, Takeyuki ^{[1
]}

Takizawa, Shinobu ^{[1
]}

Sasai, Hiroaki ^{[1
]}

机构：

[1] Osaka Univ, ISIR, Osaka 5670047, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2009年 / 82卷 / 03期

关键词：

PD(II)-SPIRO BIS(ISOXAZOLINE) CATALYST; HIGHLY ENANTIOSELECTIVE HYDROGENATION; NITROGEN-CONTAINING LIGANDS; WACKER-TYPE CYCLIZATION; CARBONYL-ENE REACTIONS; DIELS-ALDER REACTIONS; ALTERNATING COPOLYMERIZATION; PHOSPHORAMIDITE LIGANDS; COORDINATION CHEMISTRY; EFFICIENT SYNTHESIS;

D O I：

10.1246/bcsj.82.285

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 Pd-11 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.

引用

页码：285 / 302

页数：18

共 125 条

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[Anonymous], 1999, COMPREHENSIVE ASYMME, V1-3

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