Stereochemistry of 1,5-Benzothiazepin-4-one <i>S</i>‑Oxide: Insight into the Stereogenic Elements at the Sulfur Atom and Axis
Hidetsugu Tabata
Tetsuya Yoneda
Tetsuta Oshitari
Hideyo Takahashi
Hideaki Natsugari
10.1021/jo401020y.s003
https://acs.figshare.com/articles/dataset/Stereochemistry_of_1_5_Benzo_thiazepin_4_one_i_S_i_Oxide_Insight_into_the_Stereogenic_Elements_at_the_Sulfur_Atom_and_Axis/2403274
Oxidation
of 1,5-benzothiazepin-4-one (<b>5</b>-<b>A</b>)
stereoselectively afforded the <i>S</i>-oxide <b>8I</b>-<b>A</b> (a<i>S</i>,1<i>S</i>) in preference
to the diastereomer <b>8II</b>-<b>A</b> (a<i>S</i>,1<i>R</i>) affected by the remote
stereogenic axis. All the enantiomers (<b>8I</b>-<b>A</b>/<b>8I</b>-<b>B</b> and <b>8II</b>-<b>A</b>/<b>8II</b>-<b>B</b>) were separated and isolated, and
the interconversion between <b>8I</b> and <b>8II</b> (equilibrium
ratio ≈5:1) was unequivocally verified to be caused by the
rotation around the axis.
2013-06-21 00:00:00
Insight
benzo
AxisOxidation
stereoselectively
Stereochemistry
Stereogenic Elements
ratio
aS
enantiomer
equilibrium
diastereomer
stereogenic axis
preference
rotation
Sulfur Atom
Benzo
interconversion
8 II