%0 Journal Article %A Pastine, Stefan J. %A Sames, Dalibor %D 2005 %T Room Temperature Intramolecular Hydro-O-alkylation of Aldehydes:  sp3 C−H Functionalization via a Lewis Acid Catalyzed Tandem 1,5-Hydride Transfer/Cyclization %U https://acs.figshare.com/articles/journal_contribution/Room_Temperature_Intramolecular_Hydro_O_alkylation_of_Aldehydes_sp_sup_3_sup_C_H_Functionalization_via_a_Lewis_Acid_Catalyzed_Tandem_1_5_Hydride_Transfer_Cyclization/3255544 %R 10.1021/ol0522283.s001 %2 https://ndownloader.figshare.com/files/5090923 %K sequence %K Transfer %K Functionalization %K Aldehyde %K aldehyde substrates %K variety %K sterically %K mechanism %K Tandem %K scope %K transformation %K spiroketal %K tandem %K aminal %K Lewis acids %K Catalyzed %K bicyclic ketals %K limitation %K sp %K hydride %K Hydride %K Intramolecular %K transfer %K intramolecular %K bond %X 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. %I ACS Publications