Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes: sp3 C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization
- 1 November 2005
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (24), 5429-5431
- https://doi.org/10.1021/ol0522283
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 C−H bonds into C−O 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.Keywords
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