Chiral phosphoric acid and its applications of asymmetric catalytic hydrogenation

Sun Zhuoxin,J Sun,X Liu,Z Li

doi:10.1051/e3sconf/202129001008

Abstract

As an excellent representative of organic small molecular catalysts, chiral phosphoric acid played an important role in asymmetric catalytic hydrogenation. According to the skeleton of chiral phosphoric acid, the development and applications of chiral phosphoric acid were summarized. The applications of chiral phosphoric acid in asymmetric catalytic hydrogenation were introduced according to three kinds of hydrogen source systems used in chiral phosphoric acid catalytic reaction. It was found that chiral phosphoric acid has high activity and excellent selectivity. Chiral products with excellent yields and enantioselectivities were obtained in most reactions.

Highlights

In 2001, Professor Noyori, and Dr Knowles won the Nobel Prize for their outstanding contributions in asymmetric catalytic hydrogenation
It is divided into four types according to the difference of skeleton structures, which are: BINOL-type, H8-BINOL-type, SPINOL-type, VANOL-type and VAPOL-type (Figure 1).[3]
BINOL derived chiral phosphoric acids have been used in organic synthesis for nearly 50 years, their application as catalysts only started more than ten years ago

Summary

Introduction

In 2001, Professor Noyori, and Dr Knowles won the Nobel Prize for their outstanding contributions in asymmetric catalytic hydrogenation. Asymmetric catalytic hydrogenation was first catalyzed by transition metals. Compared with small molecular catalysts, transition metal catalysts have the disadvantages of high toxicity, difficult to synthesize and recover.[1] In 1989, Professor Batra first used amino acids as catalyst to realize asymmetric transfer hydrogenation without metal participation, which opened a new door for the asymmetric reduction of small molecular catalysts.[2] Subsequently, the technology of small molecular catalysis has been developed rapidly, and the types of catalysts are becoming more and more abundant. Chiral phosphoric acid is a kind of small molecular catalyst with excellent reaction activity and selectivity. It is divided into four types according to the difference of skeleton structures, which are: BINOL-type, H8-BINOL-type, SPINOL-type, VANOL-type and VAPOL-type (Figure 1).[3]

Development of chiral phosphoric acid

Asymmetric reduction catalyzed by chiral phosphoric acid

Findings

Conclusion