Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes: sp3 CH Functionalization via a Lewis Acid Catalyzed Tandem 1, 5-Hydride Transfer/Cyclization
SJ Pastine, D Sames
Index: Pastine, Stefan J.; Sames, Dalibor Organic Letters, 2005 , vol. 7, # 24 p. 5429 - 5431
Full Text: HTML
Citation Number: 99
Abstract
The scope and limitations of intramolecular hydro-O-alkylation of aldehyde substrates leading to spiroketals and bicyclic ketals and aminals is reported. The direct transformation of tertiary and sterically hindered secondary sp3 CH bonds into CO bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.
Related Articles:
2-Diethylaminoethyl esters of 1, 3-disubstituted propane-2-carboxylic acids
[Valenta, Vladimir; Holubek, Jiri; Svatek, Emil; Miller, Vladimir; Vlkova, Marie; Protiva, Miroslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 10 p. 2534 - 2544]
2-Diethylaminoethyl esters of 1, 3-disubstituted propane-2-carboxylic acids
[Valenta, Vladimir; Holubek, Jiri; Svatek, Emil; Miller, Vladimir; Vlkova, Marie; Protiva, Miroslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 10 p. 2534 - 2544]
2-Diethylaminoethyl esters of 1, 3-disubstituted propane-2-carboxylic acids
[Valenta, Vladimir; Holubek, Jiri; Svatek, Emil; Miller, Vladimir; Vlkova, Marie; Protiva, Miroslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 10 p. 2534 - 2544]
[Nguyen, John D.; Tucker, Joseph W.; Konieczynska, Marlena D.; Stephenson, Corey R. J. Journal of the American Chemical Society, 2011 , vol. 133, # 12 p. 4160 - 4163]
2-Diethylaminoethyl esters of 1, 3-disubstituted propane-2-carboxylic acids
[Valenta, Vladimir; Holubek, Jiri; Svatek, Emil; Miller, Vladimir; Vlkova, Marie; Protiva, Miroslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 10 p. 2534 - 2544]