Organic letters

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

文献索引：Pastine, Stefan J.; Sames, Dalibor Organic Letters, 2005 , vol. 7, # 24 p. 5429 - 5431

全文：HTML全文

被引用次数: 99

摘要

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.