Tetrahedron Letters

AuCl 3/AgSbF 6-catalyzed rapid epoxide to carbonyl rearrangement

V Gudla, R Balamurugan

Index: Gudla, Vanajakshi; Balamurugan, Rengarajan Tetrahedron Letters, 2012 , vol. 53, # 39 p. 5243 - 5247

Full Text: HTML

Citation Number: 20

Abstract

An efficient epoxide to carbonyl rearrangement using catalytic AuCl3/AgSbF6 has been presented. The reactions are fast and high yielding. β-Hydrogen migration takes place exclusively when hydrogen and methyl or substituted methyl groups are present at β-carbon of epoxide. When phenyl/acetyl/benzoyl and hydrogen are available at same carbon atom, migration of the former is preferred over the latter.

Related Articles:

Cleavage of carbon-carbon triple bond of alkyne via hydroiminoacylation by Rh (I) catalyst

[Jun; Lee; Choong Woon Moon; Hong Journal of the American Chemical Society, 2001 , vol. 123, # 35 p. 8600 - 8601]

The reaction of α, β-epoxy sulfoxides with lithium dimethylcuprate giving enolates: A novel synthesis of aldols

[Satoh, Tsuyoshi; Sugimoto, Atsushi; Itoh, Masayuki; Yamakawa, Koji Tetrahedron Letters, 1989 , vol. 30, # 9 p. 1083 - 1086]

Intermolecular hydroamination of alkynes catalyzed by dimethyltitanocene

[Angewandte Chemie - International Edition, , vol. 38, # 22 p. 3389 - 3391]

Probes of the active site of norepinephrine N-methyltransferase: effect of hydrophobic and hydrophilic interactions on side-chain binding of amphetamine and. alpha.- …

[Grunewald, Gary L.; Monn, James A.; Rafferty, Michael F,; Borchardt, Ronald T.; Krass, Polina Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1248 - 1250]

Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes

[Ghosh, Usha; Ganessunker, Deshanie; Sattigeri, Viswajanani J.; Carlson, Kathryn E.; Mortensen, Deborah J.; Katzenellenbogen, Benita S.; Katzenellenbogen, John A. Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 4 p. 629 - 657]

More Articles...