Diastereoselective α‑Fluorination\nof <i>N</i>-<i>tert</i>-Butanesulfinyl Imidates
Wei Huang (36889)Yun Yao (5056934)Yan-Jun Xu (639271)Chong-Dao Lu (1393924)
Abstract
A diastereoselective\nα-fluorination of <i>N</i>-<i>tert</i>-butanesulfinyl\nimidates was developed. Deprotonation\nof <i>N</i>-<i>tert</i>-butanesulfinyl imidates\nwith lithium hexamethyldisilazide generates aza-enolates that can\nbe intercepted, with excellent diastereocontrol, by the inexpensive\nelectrophilic fluorinating agent NFSI. This protocol was applied to\nthe preparation of synthetically useful <i>trans</i>-2-fluoro-cyclohexamine\nwith high enantiomeric purity (99.5% ee).
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