10.1021/ol0509080.s001
Mieczysław Ma̧kosza
Mieczysław
Ma̧kosza
Michał Barbasiewicz
Michał
Barbasiewicz
Dariusz Krajewski
Dariusz
Krajewski
Diastereoselective Synthesis of
Tetrahydrofurans via Reaction of
γ,δ-Epoxycarbanions with Aldehydes<sup>†</sup>
American Chemical Society
2005
adduct
potassium tert
presence
butoxide
Aldehyde
oxirane ring
Diastereoselective Synthesis
S N 2 process
carbanion
Tetrahydrofuran
cyclization
Epoxycarbanion
nondiastereoselective
sulfone
aldehyde
diastereoisomer
lithium
mixture
tetrahydrofuran
phenyl
diastereoselectivity
epoxybutyl
Initial formation
configuration
carbon stereocenter
diastereoselectively
2005-07-07 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Diastereoselective_Synthesis_of_Tetrahydrofurans_via_Reaction_of_Epoxycarbanions_with_Aldehydes_sup_sup_/3278557
Hydroxymethyl-substituted tetrahydrofurans were prepared with high diastereoselectivity by reaction of the carbanion derived from 3,4-epoxybutyl
phenyl sulfone with aldehydes in the presence of a mixture of lithium and potassium <i>tert-</i>butoxides. Initial formation of aldol-type adducts is
a nondiastereoselective but reversible process; thus, subsequent formation of one main diastereoisomer is controlled by the relative rates of
cyclization. The configuration of the carbon stereocenter at the oxirane ring is inverted in the course of the S<sub>N</sub>2 process, and two new centers
are created diastereoselectively.