%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