Asymmetric Baeyer-Villiger oxidation of cyclobutanones
Oxidation of substituted racemic or prochiral cyclobutanones under Sharpless conditions resulted in enatiomeric lactones with 34–75% ee.
References (20)
- et al.
Org. Magn. Res.
(1972) Org. React.
(1993)- et al.
J. Org. Chem.
(1996)et al.J. Org. Chem.
(1994) - et al.
- et al.
Organometallics
(1994) - et al.
Angew. Chem., Int. Ed. Engl.
(1994) - et al.
J. Am. Chem. Soc.
(1981) - et al.
J. Org. Chem.
(1995) - et al.
J. Am. Chem. Soc.
(1987)
Cited by (81)
5.1 Asymmetric Baeyer-Villiger Oxidation
2012, Comprehensive ChiralityPalladium-catalyzed, asymmetric Baeyer-Villiger oxidation of prochiral cyclobutanones with PHOX ligands
2011, TetrahedronCitation Excerpt :Additionally, Miller and co-workers have shown in preliminary results that chiral carboxylic acids can be used to desymmetrize prochiral ketones with modest selectivities (30 and 42% ee).13 Our interest in the development of enantioselective oxidation processes along with our extensive experience with and collection of P,N-type phosphinooxazoline (PHOX) ligands (7–13, Fig. 1)14 led us to examine the palladium-catalyzed Baeyer–Villiger oxidations of cyclic ketones. We have recently demonstrated the utility of PHOX ligands in palladium-catalyzed enantioselective decarboxylative alkylation15 and protonation reactions.16
Oxidation of cycloalkanones with hydrogen peroxide: an alternative route to the Baeyer-Villiger reaction. Synthesis of dicarboxylic acid esters
2008, TetrahedronCitation Excerpt :The problem of the development of efficient methods for the synthesis of dicarboxylic acids and their derivatives has attracted considerable attention for more than half a century, because these compounds are building blocks in the production of polyamide, polyurethane, and polyester polymers, plasticizing agents, lubricants, and anticorrosive systems. The oxidation reactions of cyclic ketones to dicarboxylic acids with nitric acid,7 potassium permanganate,8 and other oxidants in the presence of catalysts containing W,9 Ce,10 Re,11 Mn,12 Cu,10a Co,12d,e Pt,13 V,14 or Mo9b,14 were studied in detail. However, simple methods of oxidation (without the use of additional reagents) of cyclic ketones to dicarboxylic acids with hydrogen peroxide are lacking.
Rearrangements of organic peroxides and related processes
2016, Beilstein Journal of Organic ChemistryLewis Acid Catalysed Asymmetric One-Carbon Ring-Expansion of Prochiral Cyclobutanones
2023, Synthesis (Germany)