Spiro-2,2′-bichroman-based bisoxazoline (SPANbox) ligands for ZnII-catalyzed enantioselective hydroxylation of β-keto esters and 1,3-diester

被引：79

作者：

Li, Jie ^{[1
]}

Chen, Gang ^{[1
]}

Wang, Zheng ^{[1
]}

Zhang, Ruzhou ^{[1
]}

Zhang, Xumu ^{[1
,2
]}

Ding, Kuiling ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] Rutgers State Univ, Dept Chem & Chem Biol, Ctr Mol Catalysis, Piscataway, NJ 08854 USA

来源：

CHEMICAL SCIENCE | 2011年 / 2卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ALPHA-HYDROXYLATION; HYDROGENATION; BIS(OXAZOLINE); CYCLIZATION; COMPLEXES; SPANPHOS;

D O I：

10.1039/c0sc00607f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new type of spiro bisoxazoline ligand (SPANbox) has been developed on the basis of the spiro-2,2'-bichroman motif and bisoxazoline chelating units. The Zn(II) complexes of SPANbox showed excellent activity (98-99% yield) and enantioselectivity (90-98% ee) in the catalysis of hydroxylation of various beta-keto esters and 1,3-diester with catalyst loading of 0.1-5 mol%. The performance of SPANbox in the present catalytic system was found to be significantly superior to the commonly used classic bisoxazoline ligands, such as (R,R)-Ph-Box or (S,S)-tBu-PyBox, indicating the advantage of the present spiro ligand skeleton.

引用

页码：1141 / 1144

页数：4