jo8b02375_si_001.pdf (2.01 MB)
Diastereoselective α‑Fluorination of N-tert-Butanesulfinyl Imidates
journal contribution
posted on 2018-11-08, 17:35 authored by Wei Huang, Yun Yao, Yan-Jun Xu, Chong-Dao LuA diastereoselective
α-fluorination of N-tert-butanesulfinyl
imidates was developed. Deprotonation
of N-tert-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 trans-2-fluoro-cyclohexamine
with high enantiomeric purity (99.5% ee).