The Baeyer-Villiger reaction of 23-oxosapogenins

The Baeyer-Villiger reaction: solvent effects on reaction mechanisms.

This study focuses on the Baeyer-Villiger reaction of propanone and performic acid, with formic acid as catalyst. Continuum solvation methods (EIF-PCM and CPCM) and two density functionals (B3LYP and MPWB1K) are used to study solvent effects on two types of reaction mechanisms: concerted non-ionic and stepwise ionic. The ionic mechanism is the one found in most organic chemistry textbooks; it b...

The Baeyer-Villiger reaction: new developments toward greener procedures.

Crystal structure of a Baeyer-Villiger monooxygenase.

Flavin-containing Baeyer-Villiger monooxygenases employ NADPH and molecular oxygen to catalyze the insertion of an oxygen atom into a carbon-carbon bond of a carbonylic substrate. These enzymes can potentially be exploited in a variety of biocatalytic applications given the wide use of Baeyer-Villiger reactions in synthetic organic chemistry. The catalytic activity of these enzymes involves the...

Conversion of Furans by Baeyer-Villiger Monooxygenases

Various furans are considered as valuable platform chemicals as they can be derived from plant biomass. Yet, for their exploitation, follow-up chemistry is required. Here we demonstrate that Baeyer-Villiger monooxygenases (BVMOs) can be used as biocatalysts for the selective oxidation of several furans, including 5-(hydroxymethyl) furfural (HMF) and furfural. A total of 15 different BVMOs were ...

The role of acid catalysis in the Baeyer-Villiger reaction. A theoretical study.

Quantum mechanical calculations at the B3LYP/6-311+G(d,p) level have examined the overall mechanism of the Baeyer-Villiger (BV) reaction with peroxyacetic acid. A series of reactions that include both the addition step and the subsequent alkyl group migration step included ketones, acetone, t-butyl methyl ketone, acetophenone, cyclohexyl methyl ketone, and cyclohexyl phenyl ketone. The combined...