Synthesis of P- and S-Stereogenic Compounds via Enantioselective C–H Functionalization

Pu-Fan Qian; Jun-Yi Li; Tao Zhou; Bing-Feng Shi

doi:10.1055/a-1802-6793

Synthesis, Table of Contents

Synthesis 2022; 54(21): 4784-4794
DOI: 10.1055/a-1802-6793

special topic

Asymmetric C–H Functionalization

Synthesis of P- and S-Stereogenic Compounds via Enantioselective C–H Functionalization

Pu-Fan Qian ‡

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. of China

,

Jun-Yi Li‡

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. of China

,

Tao Zhou∗

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. of China

,

Bing-Feng Shi ∗

^aCenter of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, P. R. of China

^bGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001, P. R. of China

^cSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan, 453007, P. R. of China

› Author Affiliations

Abstract

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Abstract

Transition metal-catalyzed enantioselective C–H functionalization has emerged as an efficient and powerful strategy to access various chiral molecules. Recently, this strategy has also provided a complementary pathway to the construction of P- and S-stereogenic compounds. In this short review, we summarize the development and applications of various catalytic systems: Pd(II)/mono-N-protected amino acids (MPAA), Pd(0)/trivalent phosphorus chiral ligands, chiral cyclopentadienyl-ligated metal catalysts [Cp^xM(III)] (M = Rh, Ir), half-sandwich d⁶ Ir(III) and Ru(II) with a chiral carboxylic acid (CCA) ligand, Ir(I)/chiral bidentate boryl ligand, and Ir(I)/chiral cation, for accessing these chiral compounds via enantioselective C–H functionalization.

1 Introduction

2 Pd(II)/Mono-N-protected Amino Acids

3 Pd(0)/Trivalent Phosphorus Chiral Ligands

4 Chiral Cyclopentadienyl-Ligated Metal Catalysts [Cp^xM(III)] (M = Rh, Ir)

5 Half-sandwich d⁶ Ir(III) and Ru(II) with a Chiral Carboxylic Acid (CCA) Ligand

6 Ir(I)/Chiral Bidentate Boryl Ligand

7 Ir(I)/Chiral Cation

8 Conclusion and Outlook

Key words

enantioselectivity - C–H functionalization - P- and S-stereogenic compounds - chiral ligands - transition metals

Full Text

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