THE BAEYER-VILLIGER OXIDATION OF 7-ALKYLIDENEBICYCLO[2.2.1]HEPTENONE

Baeyer–Villiger oxidation of norbornan-7-ones: long-range substituent effects on regioselectivity

Baeyer–Villiger (BV) oxidation is a commonly employed reaction for the transformation of ketones into esters/lactones by organic peroxy acids or hydrogen peroxide. The BV reaction is extensively used since when it is suitably juxtaposed in a synthetic sequence, it can lead to the shortening of carbon chains, amplification of functionality in carbocyclic rings and chains, and transformation of c...

An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation.

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 ...

A Carbonate-Forming Baeyer-Villiger Monooxygenase

Despite the remarkable versatility displayed by flavin-dependent monooxygenases (FMOs) in natural product biosynthesis, one notably missing activity is the oxidative generation of carbonate functional groups. We describe a multifunctional Baeyer-Villiger monooxygenase, CcsB, which catalyzes the formation of an in-line carbonate in the macrocyclic portion of cytochalasin E. This study expands th...