A new and efficient chemoenzymatic route to both enantiomers of α′-acetoxy and α′-hydroxy-α-methoxy cyclic enones

Demir, Ayhan S.; Caliskan, Zerrin Zerenler; Aydin, A. Ebru; Bicer, Isil

doi:10.1016/j.tetasy.2006.01.025

Cited by 6 publications

(1 citation statement)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is suggested that manganese(III) acetate causes the generation of C-radicals from ketones followed by the acetoxylation of these radicals. In this reaction, Mn(OAc) 3 [ 204 – 210 ] or acetic acid [ 209 – 210 ], which was used as the co-solvent, can serve as the source of the acetoxy group. The synthesis is usually performed in benzene.…”

Section: Reviewmentioning

confidence: 99%

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Krylov

Vil

Terent’ev

2015

Beilstein J. Org. Chem.

171

View full text Add to dashboard Cite

SummaryThe present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

show abstract

Section: Reviewmentioning

confidence: 99%

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Krylov

Vil

Terent’ev

2015

Beilstein J. Org. Chem.

171

View full text Add to dashboard Cite

show abstract

Manganese(III)-promoted reactions for formation of carbon–heteroatom bonds

2009

View full text Add to dashboard Cite

Manganese(III) reagent is an important one- electron oxidant for initiation of free-radical reactions and formation of carbon-carbon bonds. The reactions are usually carried out under mild conditions, have high regio- and stereo-selectivities, and good functional group tolerance. Summarized in this article are the developments of manganese (III)-based reactions for the formation of carbon-heteroatom bonds including carbon-oxygen, carbon-phosphorus, carbon-sulfur, and carbon-nitrogen bonds, and their applications for the synthesis of related heterocyclic systems.

show abstract