jo401020y_si_002.cif (44.56 kB)
Stereochemistry of 1,5-Benzothiazepin-4-one S‑Oxide: Insight into the Stereogenic Elements at the Sulfur Atom and Axis
dataset
posted on 2013-06-21, 00:00 authored by Hidetsugu Tabata, Tetsuya Yoneda, Tetsuta Oshitari, Hideyo Takahashi, Hideaki NatsugariOxidation
of 1,5-benzothiazepin-4-one (5-A)
stereoselectively afforded the S-oxide 8I-A (aS,1S) in preference
to the diastereomer 8II-A (aS,1R) affected by the remote
stereogenic axis. All the enantiomers (8I-A/8I-B and 8II-A/8II-B) were separated and isolated, and
the interconversion between 8I and 8II (equilibrium
ratio ≈5:1) was unequivocally verified to be caused by the
rotation around the axis.
