Abstract

A great number of reports have described asymmetric catalytic Henry reactions using nitromethanes as pronucleophiles, but far more challenging is diastereoselective catalytic Henry reactions using substituted higher nitroalkanes instead of nitromethane to generate chiral β-nitro alcohol scaffolds with four adjacent stereogenic centers in a one-pot operation. This review summarizes the current state and applications of such reactions involving complex nitroalkane coupling with various carbonyl compounds for resolving double chiral centers with high enantio- and diastereoselectivities.

Highlights

  • Over the past two decades, asymmetric catalytic Henry reactions have been established as an integral part of asymmetric catalysis.[1,2] During this period, a lot of reviews using nitromethanes as pronucleophiles have been reported

  • This review summarizes the current state and applications of such reactions involving complex nitroalkane coupling with various carbonyl compounds for resolving double chiral centers with high enantio- and diastereoselectivities

  • In 1998, he moved to Fudan University as a full professor. His current research focuses on the development of new asymmetric catalysts, asymmetric total synthesis of natural products, process chemistry and computer assisted mechanism-based drug design (CADD)

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Summary

Introduction

Over the past two decades, asymmetric catalytic Henry reactions have been established as an integral part of asymmetric catalysis.[1,2] During this period, a lot of reviews using nitromethanes as pronucleophiles have been reported. In 1998, he moved to Fudan University as a full professor His current research focuses on the development of new asymmetric catalysts, asymmetric total synthesis of natural products, process chemistry and computer assisted mechanism-based drug design (CADD). Fen-Er Chen has been a visiting professor at numerous prestigious universities, including Washington University, King's College London, etc He is currently a member of Academician of Chinese Academy of Engineering. The present review aims to describe the impressive growth in this rapidly expanding eld It examines the current state of direct asymmetric catalytic Henry reactions involving higher nitroalkanes rather than simple nitromethanes coupling with various carbonyl compounds that control the stereochemistry at double chiral centers. The discussion is divided in two based on the type of catalyst: metal/chiral ligand complex-based reactions and organocatalytic reactions

Rare earth-catalyzed asymmetric diastereoselective Henry reaction
Lanthanum-based catalysis
Catalysis by a neodymium–sodium heterobimetallic complex
Copper-catalyzed asymmetric diastereoselective Henry reaction
Chiral imidazoline ligands
Chiral Schiff-base ligands
Chiral diamines ligands
Other type of chiral ligands
Cobalt-catalyzed asymmetric diastereoselective Henry reaction
Guanidine derived organocatalysts
Tetraaminophosphonium salt derived organocatalysts
Findings
Conclusions
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