Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)

被引：12

作者：

Liu Xu ^{[1
]}

Han ZhaoBin ^{[1
]}

Wang Zheng ^{[1
]}

Ding KuiLing ^{[1
]}

机构：

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

来源：

SCIENCE CHINA-CHEMISTRY | 2014年 / 57卷 / 08期

基金：

中国国家自然科学基金;

关键词：

bis(diarylvinylphosphine oxide); iridium; asymmetric hydrogenation; PCP-type chiral pincer ligands; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; HIGHLY ENANTIOSELECTIVE HYDROGENATION; PINCER COMPLEXES; METHYL ISOCYANOACETATE; CARBONYL-COMPOUNDS; ALDOL REACTION; DIARYLPHOSPHINES; LIGANDS; PCP;

D O I：

10.1007/s11426-014-5134-7

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed into the corresponding borane-protected chiral PCP-type pincer ligand 7a with high enantiomeric excess, exemplifying a viable synthetic route to optically active chiral PCP pincer ligands.

引用

页码：1073 / 1078

页数：6

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