Recent Developments in Epoxide Preparation

Abstract

This review will present recent achievements in the use of novel reactants and synthetic procedures for the transformation of substrates into epoxide derivatives. This will include both classical chemical methods using novel catalysts and/or cleaner methodologies, and enzymatic preparations using enzymes or cells. Special attention is paid to the preparation of chiral compounds. A comparison of the advantages and disadvantages of the different preparations is also included.

Biocatalytic Epoxidation for Green Synthesis

“…Enantiopure epoxides, in particular, play an important role in organic synthesis and the pharmaceutical industry [3,4]. In recent decades, there have been enormous advances in the development of catalysts, including chemical catalysts and biocatalysts, for the production of chiral epoxides [5][6][7][8][9][10].…”

“…Direct epoxidation of alkenes and kinetic resolution of racemic epoxides are the two major approaches for the synthesis of chiral epoxides [5][6][7][8][9]. Although great success has been achieved in the hydrolytic kinetic resolution of epoxides [11][12][13][14], asymmetric epoxidation of alkenes remains the most attractive approach due to better atom efficiency of direct incorporation of the C⏤O functional group [15,16].…”

Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

“…The versatility of the epoxide is attributed to the oxirane function that can be opened by various nucleophiles or undergo elimination, reduction or rearrangements to a multitude of more elaborate intermediates with the retention or inversion of chirality [5][6][7].…”

“…Several reviews on the preparation of chiral epoxides have been published [3,7,8,[22][23][24][25][26]. This review does not seek to provide a comprehensive list of all kinds of synthetic/enzymatic methods, but rather to emphasize the potential of biocatalysis in the preparation of chiral epoxides.…”

Catalytic Epoxidation and Sulfoxidation Activity of a Dioxomolybdenum(VI) Complex Bearing a Chiral Tetradentate Oxazoline Ligand

“…Epoxides are key building blocks in organic chemistry for the functionalization of substrates and the production of a wide variety of chemicals, such as alcohols, carbonyl compounds, ethers, and amino alcohols [1,2]. Their synthesis generally involves a catalyzed oxidation of carbon-carbon double bonds with peroxides [3][4][5][6].…”