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Letter

Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes: sp³ C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization

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Stefan J. Pastine and Dalibor Sames*

Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027

Org. Lett., 2005, 7 (24), pp 5429–5431

DOI: 10.1021/ol0522283

Publication Date (Web): November 4, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, sames@chem.columbia.edu

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.

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Published In Issue November 24, 2005
Received September 14, 2005

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Letter

Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes: sp³ C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization