Baeyer-Villiger-type oxidation of an isoindolo[1,2-b][3]benzazepine derivative

Bernhard, Heinz O.; Reed, Joseph; Snieckus, Victor

doi:10.1021/jo00426a040

Cited by 13 publications

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“…The most plausible mechanism for the conversion of 60 to 64 involves the intermediacy of aminoepoxide 62. R-Amino epoxides have been invoked as intermediates in the oxidation of enamines [40][41][42][43][44] and in the rearrangement of R-halo ketones and amines to R-amino ketones. 45 These highly reactive three-ring heterocycles undergo facile rearrangement and the specific product isolated has been found to be dependent on the nature of the substituents on both the epoxide and nitrogen atom.…”

Section: Resultsmentioning

confidence: 99%

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Rhodium(II)-Catalyzed Cyclization of Amido Diazo Carbonyl Compounds

et al. 2000

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A series of acyclic diazo ketoamides were prepared from N-benzoyl-N-alkylaminopropanoic acids and were treated with a catalytic amount of rhodium(II) acetate. The resultant carbenoids underwent facile cyclization onto the neighboring amide carbonyl oxygen atom to generate seven-membered carbonyl ylide dipoles. Subsequent collapse of the dipoles with charge dissipation produce bicyclic epoxides which undergo further reorganization to give substituted 5-hydroxydihydropyridones in good yield. Depending on the nature of the substituent groups, it was possible to trap some of the initially formed carbonyl ylide dipoles with a reactive dipolarophile such as DMAD. In other cases, cyclization of the dipole to the epoxide is much faster than bimolecular trapping. A related cyclization/rearrangement sequence occurred when diazo ketoamides derived from the cyclic pyrrolidone and piperidone ring systems were subjected to catalytic quantities of Rh(II) acetate. With these systems, exclusive O-cyclization of the amido group onto the carbenoid center occurs to generate a seven-ring carbonyl ylide dipole. Starting materials are easily prepared, and the cascade sequence proceeds in good yield and does not require special precautions. The overall procedure represents an efficient one-pot approach toward the synthesis of various indolizidine and quinolizidine ring systems.

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Section: Resultsmentioning

confidence: 99%

“…The most plausible mechanism for the conversion of 60 to 64 involves the intermediacy of aminoepoxide 62 . α-Amino epoxides have been invoked as intermediates in the oxidation of enamines − and in the rearrangement of α-halo ketones and amines to α-amino ketones .…”

Section: Resultsmentioning

confidence: 99%

Rhodium(II)-Catalyzed Cyclization of Amido Diazo Carbonyl Compounds

et al. 2000

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“…However, attempts to hydrolyze the thioenol ether yielded only the enelactam (100) familiar from the Snieckus approach (refer to Scheme 30). 33 Scheme 57. Photocyclization of a benzyl t-butyl thioether.…”

Section: Scheme 56 Preparation Of a Benzyl T-butyl Thioether Photocymentioning

confidence: 99%

The aporhoeadane alkaloids

Leonard¹

2012

Arkivoc

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TheBaeyer–VilligerOxidation of Ketones and Aldehydes

1993

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The oxidative conversion of alicyclic ketones into lactones with permonosulfuric acid was discovered by Baeyer and Villiger in 1899, and in their honor the general process by which ketones are converted into esters or lactones is now known as the Baeyer–Villiger reaction. The literature on this synthetically useful process has been reviewed comprehensively through 1953 in Volume 9 of Organic Reactions , and less comprehensive reviews of the reaction have appeared since then. More recent investigations have led to the development of new synthetic reagents, to improvements in experimental reaction conditions, and to a better understanding of regiochemical and stereochemical aspects of the reaction. Baeyer–Villiger reactions now often can be carried out with functional group chemoselectivity and regiochemical control. Although the recent removal from commerce of 90% hydrogen peroxide and reagents based upon this oxidant are a setback to Baeyer–Villiger reaction methodology, alternative reagents, catalysts, and methods described in this review are available to fill the gaps. The definition of the Baeyer–Villiger reaction is somewhat fuzzy, and can be considered to include both ketones and aldehydes. In addition to the traditional use of organic and inorganic peracids as oxidants, examples of oxygen insertion reactions using hydrogen peroxide, alkyl peroxides, and several metal ion oxidants are considered to fall within the scope of this chapter and are included in the tabular survey.

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Baeyer-Villiger-type oxidation of an isoindolo[1,2-b][3]benzazepine derivative

Abstract: N -b e nzoyl-~-(4,5-dimethoxy-2-hydroxy)phenethylamine, 61177-94-4.

Cited by 13 publications

References 1 publication

Rhodium(II)-Catalyzed Cyclization of Amido Diazo Carbonyl Compounds

Rhodium(II)-Catalyzed Cyclization of Amido Diazo Carbonyl Compounds

The aporhoeadane alkaloids

TheBaeyer–VilligerOxidation of Ketones and Aldehydes

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