Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution

被引：175

作者：

Bhat, Vikram ^{[1
]}

Wang, Su ^{[1
]}

Stoltz, Brian M. ^{[1
]}

Virgil, Scott C. ^{[1
]}

机构：

[1] CALTECH, Caltech Ctr Catalysis & Chem Synth, Warren & Katharine Schlinger Lab Chem & Chem Engn, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 45期

关键词：

N CHELATING LIGAND; AXIALLY CHIRAL BIARYLS; HYDROBORATION; COMPLEXES; CATALYSTS;

D O I：

10.1021/ja409383f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A palladium-catalyzed, atroposelective C-P coupling process has been developed for the asymmetric synthesis of QUINAP and its derivatives in high enantiomeric excess. Bromide, triflate (OTf) and 4-methanesulfonylbenzenesulfonate (OSs) precursors were studied, leading in the case of the triflate to a novel dynamic kinetic resolution involving isomerization of an arylpalladium intermediate. The operationally simple methods described in this communication afford these important ligands in good to high yields and selectivity using low catalyst loading (<= 3 mol % Pd).

引用

页码：16829 / 16832

页数：4

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