Vol.:(0123456789)
Topics in Current Chemistry (2019) 377:23
https://doi.org/10.1007/s41061-019-0249-0
1 3
REVIEW
Recent Advances in First‑Row Transition Metal/Chiral
Phosphoric Acid Combined Catalysis
Gui‑Chun Fang
1
· Yong‑Feng Cheng
1
· Zhang‑Long Yu
1
· Zhong‑Liang Li
2
·
Xin‑Yuan Liu
1
Received: 29 April 2019 / Accepted: 16 August 2019 / Published online: 28 August 2019
© Springer Nature Switzerland AG 2019
Abstract
Since the pioneering independent reports of Akiyama and Terada, the use of chiral
phosphoric acids (CPAs) and derivatives as a versatile tool for asymmetric synthesis
with good reactivity, regioselectivity, diastereoselectivity and enantioselectivity has
emerged, forming an important part of the implementation of asymmetric counteranion-directed catalysis reported to date. In these achievements, the combination of
metals with CPAs has enabled various catalytic modes beyond the scope of typical
acid catalysis, such as relay catalysis, ion-pairing catalysis, and binary acid catalysis.
The first-row transition metals (Sc–Zn) are considered to be sustainable transition
metals and have received a great deal of attention. These naturally abundant metals
display excellent Lewis acidity and function as powerful redox catalysts in synthesis
involving both one and two-electron transfers. Hence, in this chapter, we summarize
recent advances in the development of asymmetric reactions using a combination of
first-row transition metals and CPAs. Furthermore, we provide a detailed discussion
of the mechanisms involved in order to understand the interaction of the metal/phosphate and the origins of the asymmetric control of the transformations.
Keywords Asymmetric catalysis · First-row transition metals · Chiral phosphoric
acids · Relay catalysis · Binary-acid catalysis · Enantioselectivity
* Xin-Yuan Liu
liuxy3@sustech.edu.cn
1
Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science
and Technology, Shenzhen 518055, China
2
SUSTech Academy for Advanced Interdisciplinary Studies, Southern University of Science
and Technology, Shenzhen 518055, China
Reprinted from the journal
153
Chapter 7 was originally published as Fang, G-C., Cheng, Y-F., Yu, Z-L., Li, Z-L. & Liu, X-Y. Topics in
Current Chemistry (2019) 377: 23. https://doi.org/10.1007/s41061-019-0249-0.
Topics in Current Chemistry (2019) 377:23
https://doi.org/10.1007/s41061-019-0249-0
1 3
REVIEW
Recent Advances in First‑Row Transition Metal/Chiral
Phosphoric Acid Combined Catalysis
Gui‑Chun Fang
1
· Yong‑Feng Cheng
1
· Zhang‑Long Yu
1
· Zhong‑Liang Li
2
·
Xin‑Yuan Liu
1
Received: 29 April 2019 / Accepted: 16 August 2019 / Published online: 28 August 2019
© Springer Nature Switzerland AG 2019
Abstract
Since the pioneering independent reports of Akiyama and Terada, the use of chiral
phosphoric acids (CPAs) and derivatives as a versatile tool for asymmetric synthesis
with good reactivity, regioselectivity, diastereoselectivity and enantioselectivity has
emerged, forming an important part of the implementation of asymmetric counteranion-directed catalysis reported to date. In these achievements, the combination of
metals with CPAs has enabled various catalytic modes beyond the scope of typical
acid catalysis, such as relay catalysis, ion-pairing catalysis, and binary acid catalysis.
The first-row transition metals (Sc–Zn) are considered to be sustainable transition
metals and have received a great deal of attention. These naturally abundant metals
display excellent Lewis acidity and function as powerful redox catalysts in synthesis
involving both one and two-electron transfers. Hence, in this chapter, we summarize
recent advances in the development of asymmetric reactions using a combination of
first-row transition metals and CPAs. Furthermore, we provide a detailed discussion
of the mechanisms involved in order to understand the interaction of the metal/phosphate and the origins of the asymmetric control of the transformations.
Keywords Asymmetric catalysis · First-row transition metals · Chiral phosphoric
acids · Relay catalysis · Binary-acid catalysis · Enantioselectivity
* Xin-Yuan Liu
liuxy3@sustech.edu.cn
1
Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science
and Technology, Shenzhen 518055, China
2
SUSTech Academy for Advanced Interdisciplinary Studies, Southern University of Science
and Technology, Shenzhen 518055, China
Reprinted from the journal
153
Chapter 7 was originally published as Fang, G-C., Cheng, Y-F., Yu, Z-L., Li, Z-L. & Liu, X-Y. Topics in
Current Chemistry (2019) 377: 23. https://doi.org/10.1007/s41061-019-0249-0.