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Diastereoselective α‑Fluorination of N-tert-Butanesulfinyl Imidates

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journal contribution
posted on 08.11.2018, 17:35 by Wei Huang, Yun Yao, Yan-Jun Xu, Chong-Dao Lu
A 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).