Asymmetric Baeyer-Villiger oxidation

In view of the requirement for cofactor regeneration these reactions are generally performed with whole microbial cells in a fermentation mode. Degrada- 

The enzyme catalyzed hydrolysis of the lactone and subsequent oxidation are unwanted side-reactions, obviously. Several yeasts [316] and E. coli [317] have 

The first example of a dynamic kinetic resolution involving a CHMO-cata-lyzed BV oxidation was recently reported (Fig. 4.116) [321]. The reaction was performed with whole cells of CHMO-containing recombinant E. coli sp. at pH 9. Under these conditions the ketone substrate underwent facile racemization, 

When comparing homogeneous and heterogeneous catalysts, clearly homogeneous systems take the lead. In addition, heterogeneous systems have the disad- 

When comparing chemical and biocatalytic methods, one could say that, especially for asymmetric oxidations, enzymatic methods enter the scene. This is most evident in the area of asymmetric Baeyer-Villiger oxidation, where biocatalysts take the lead and homogeneous chiral catalysts lag far behind in terms of ee values. Significant progress can be expected in the area of biocatalysis due to the advancement in enzyme production technologies and the possibility of tailor-made enzymes. 

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SYNTHESIS OF 2-(PHOSPHINOPHENYL)PYRINDINE LIGAND AND ITS APPLICATION TO PALLADIUM-CATALYZED ASYMMETRIC BAEYER-VILLIGER OXIDATION OF PROCHIRAL CYCLOBUTANONES... 

The asymmetric Baeyer-Villiger oxidation using a palladium complex of 2-(phosphinophenyl)pyridine ligand provides a useful procedure for the synthesis... 

SCHEME 171. Titanium-catalyzed asymmetric Baeyer-Villiger oxidation of cyclobutanones... 

SCHEME 172. Zirconium-mediated asymmetric Baeyer-Villiger oxidation... 

TABLE 32. Results of the aluminum-catalyzed asymmetric Baeyer-Villiger oxidation using chiral BINOL ligand and achiral and chiral hydroperoxides... 

Incorporation of substituted BINOL ligands improved the enantioselectivity of asymmetric Baeyer-Villiger oxidations of prochiral cyclobutanones with CHP and... 

Figure 20.6 Large-scale biocatalytic asymmetric Baeyer-Villiger oxidations.

Hilker, L, Alphand. V., Wohlgemuth, R. and Furstoss, R. (2004) Microbial transformations 56. Preparative scale asymmetric Baeyer-Villiger oxidation using a highly productive two-in-one ... 

Asymmetric Baeyer-Villiger oxidation reaction In 1994, Bolm et al used chiral Cu and Ni complexes (7.23) in catalytic amount with different oxidation systems. 

Alphand, V., Furstoss, R. Asymmetric Baeyer-Villiger oxidation using biocatalysis. Asymmetric Oxidation Reactions). 2001,214-227... 

Bolm, C., Luong, T. K. K., Beckmann, O. Oxidation of carbonyl compounds asymmetric Baeyer-Villiger oxidation. Asymmetric Oxidation Reactions). 2001,147-151... 

Lopp, M., Paju, A., Kanger, T., Pehk, T. Asymmetric Baeyer-Villiger oxidation of cyclobutanones. Tetrahedron Lett. 1996, 37, 7583-7586. 

Miyake, Y., Nishibayashi, Y., Uemura, S. Asymmetric Baeyer-Villiger oxidation of cyclic ketones using chiral organoselenium catalysts. Bull. Chem. Soc. Jpn. 2002, 75, 2233-2237. 

Asymmetric Baeyer-Villiger oxidation of prochiral ketones to optically active lactones 04IZV1784. 

Baeyer-Villiger oxidation as indicated by Strukul and coworkers. Reaction of K2PtCl4 and 6-methoxysalicylaldehyde in the presence of 2,2 -bis(diphenylphosphino)-l,l -binaphthyl (BINAP) gives acylplatiumn complexes, which in the presence of perchloric acid catalyzes the asymmetric Baeyer-Villiger oxidation with hydrogen peroxide (equation 83). ... 

The large-scale resolution of racemic 2-alkanols to enantiomerically pure (R-)-and (S-t-)-alkanols by lipase shows environmental, health and safety advantages of biocatalysis compared with nonenzymatic syntheses. The biocatalytic Baeyer-Villi-ger oxidation of racemic bicyclo[3.2.0]-hept-2-en-6-one to enantiomerically pure 2-oxabicyclo[3.3.0]-oct-6-en-3-one and 3-oxabicyclo[3.3.0]-oct-6-en-2-one by CHMO represents an asymmetric Baeyer-Villiger oxidation. 

Copper-Catalyzed Asymmetric Baeyer-Villiger Oxidation. ... 

Scheme 23.30. Asymmetric Baeyer-Villiger oxidation of meso, chiral and four-membered ring cyclic ketones with H2O2 mediated by a Pt(II) catalyst bearing an alropoisomeric diphosphine ligand.

Using water as the solvent also increased the selectivity in the asymmetric Baeyer-Villiger oxidation of cychc six- and four-membered ring ketones. In particular, the use of surfactants under micellar conditions allowed i) the direct solubilization of otherwise water insoluble complexes and ii) the increase of... 

Scheme 23.41. The asymmetric Baeyer-Villiger oxidation of 3-substituted cyclobutanones chiral cyclobutanones with H2O2 mediated by a Co(II)salen catalyst benefits greatly from the employment of micellar media instead of common organic media.

Colladon, M., Scarso, A. and Strukul, G. (2006). TaUoring Pt(ll) Chiral Catalyst Design for Asymmetric Baeyer-Villiger Oxidation of CycUc Ketones with Hydrogen Peroxide, Synlett, 20, pp. 3515-3520. 

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