Aqueous olefin metathesis: recent developments and applications.

Valerio Sabatino,Thomas R Ward

doi:10.3762/bjoc.15.39

Abstract

Olefin metathesis is one of the most powerful C–C double-bond-forming reactions. Metathesis reactions have had a tremendous impact in organic synthesis, enabling a variety of applications in polymer chemistry, drug discovery and chemical biology. Although challenging, the possibility to perform aqueous metatheses has become an attractive alternative, not only because water is a more sustainable medium, but also to exploit biocompatible conditions. This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology.

Highlights

Olefin metathesis represents a versatile synthetic tool for the construction of carbon–carbon bonds [1,2,3,4,5,6,7,8,9]
This review focuses on the recent improvements of olefin metathesis in aqueous media and the resulting applications in bioinorganic chemistry and chemical biology
Cavity-size engineered artificial metalloenzymes (ArMs) are the first example of biohybrid catalysts able to catalyze all three main olefin metathesis reactions (RCM, Ring-opening metathesis polymerization (ROMP) and CM) [72]

Summary

Introduction

Olefin metathesis represents a versatile synthetic tool for the construction of carbon–carbon bonds [1,2,3,4,5,6,7,8,9]. Blechert and Raines both performed RCM reactions with the benchmark substrate 21 in mixtures of water/organic solvent at room temperature in air (Table 2). Scheme 6 displays the RCM of selected substrates with G-II as catalyst in the presence of PTS as surfactant.

Results

Conclusion