Diastereoselective α‑Fluorination
of <i>N</i>-<i>tert</i>-Butanesulfinyl Imidates
Wei Huang
Yun Yao
Yan-Jun Xu
Chong-Dao Lu
10.1021/acs.joc.8b02375.s002
https://acs.figshare.com/articles/dataset/Diastereoselective_Fluorination_of_i_N_i_-_i_tert_i_-Butanesulfinyl_Imidates/7315637
A diastereoselective
α-fluorination of <i>N</i>-<i>tert</i>-butanesulfinyl
imidates was developed. Deprotonation
of <i>N</i>-<i>tert</i>-butanesulfinyl imidates
with lithium hexamethyldisilazide generates aza-enolates that can
be intercepted, with excellent diastereocontrol, by the inexpensive
electrophilic fluorinating agent NFSI. This protocol was applied to
the preparation of synthetically useful <i>trans</i>-2-fluoro-cyclohexamine
with high enantiomeric purity (99.5% ee).
2018-11-08 17:35:38
butanesulfinyl imidates
trans -2- fluoro-cyclohexamine
diastereoselective α- fluorination
electrophilic fluorinating agent NFSI
tert