Synthesis of Chiral Tridentate Ligands with a Ferrocene Framework and Their Applications in Ir-Catalyzed Asymmetric Hydrogenation
Xin Lin , Fanfu Guan , Jialin Wen , Pan-Lin Shao , Xumu Zhang
Progress in Chemistry ›› 2020, Vol. 32 ›› Issue (11) : 1680 -1696.
In this review, the synthesis and application of a series of tridentate ligands, such as f-amphox, f-ampha, f-amphol and f-amphamide, bearing ferrocene skeleton are introduced. The corresponding iridium complex based on these chiral P-N ligands can catalyze(functionalized) ketones with high TON(up to 1 000 000), excellent conversion(>99%) and enantioselectivity(>99% ee). The application of the f-series ligands has successfully realized the asymmetric synthesis of many chiral pharmaceutical intermediates such as Dinopramine, Phenylephrine and Salbutamol. These approaches are more efficient, generating less by-products and lower industrial emissions compared with the traditional routes.
1 Introduction
2 History of tridentate ferrocene ligands
2.1 The development of tridentate ligands
2.2 Special properties of ferrocene skeleton
2.3 Representative ligands containing ferrocene framework
3 f-amphox
3.1 The synthesis of f-amphox
3.2 Application of f-amphox in asymmetric hydrogenation
4 f-amphol
4.1 The synthesis of f-amphol
4.2 Application of f-amphol in asymmetric hydrogenation
5 f-ampha
5.1 The synthesis of f-ampha
5.2 Application of f-amphol in asymmetric hydrogenation
6 f-amphamide
6.1 The synthesis of f-amphamide
6.2 Application of f-amphamide in asymmetric hydrogenation
7 New mechanism insight about asymmetric hydrogenation
7.1 Hydrogenation mechanism of N—H structure
7.2 The chiral sources of f series
7.3 Transition state model of asymmetric hydrogenation
8 Conclusion and outlook
ferrocene / f-amphox / f-ampha / f-amphol / f-amphamide / asymmetric hydrogenation
the Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis(ZDSYS20190902093215877)
the Science, Technology and Innovation Commission of Shenzhen(JCYJ20190809160211372)
/
| 〈 |
|
〉 |
PDF
