Nickel-Catalyzed Asymmetric Ullmann Coupling for the Synthesis of Axially Chiral Tetra-ortho-Substituted Biaryl Dials

被引：50

作者：

Chen, Wen-Wen ^{[1
]}

Zhao, Qian ^{[1
]}

Xu, Ming-Hua ^{[1
,2
]}

Lin, Guo-Qiang ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ENANTIOMERICALLY PURE; 1,1'-BINAPHTHYL-2,2'-DICARBOXYLIC ACID; OPTICAL RESOLUTION; CYCLIC TRANS-1,2-DIOLS; NATURAL-PRODUCTS; TANDEM REACTION; EFFICIENT; COMPLEXES; HYDROGENATION; LIGANDS;

D O I：

10.1021/ol1000632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of nickel-catalyzed asymmetric Ullmann coupling of bis-ortho-substituted arylhalides is described. With the chiral BINOL-based monodentate phosphoramidite ligand, the reaction allows atropoenantioselective synthesis of a series of axially chiral tetra-ortho-substituted biaryl dials. By taking advantage on this asymmetric Ullman coupling as a key stereogenic axis-forming reaction, the formal synthesis of (+)-isoschizandrin was accomplished.

引用

页码：1072 / 1075

页数：4

共 68 条

[1] Efficient synthesis of 1,1′-binaphthyl and 2,2′-bi-o-tolyl-2,2′-bis(oxazoline)s and preliminary use for the catalytic asymmetric allylic oxidation of cyclohexene [J].