Diastereoselective α‑Fluorination
of N-tert-Butanesulfinyl Imidates
Posted on 2018-11-08 - 17:35
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).
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Huang, Wei; Yao, Yun; Xu, Yan-Jun; Lu, Chong-Dao (2018). Diastereoselective α‑Fluorination
of N-tert-Butanesulfinyl Imidates. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b02375
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AUTHORS (4)
WH
Wei Huang
YY
Yun Yao
YX
Yan-Jun Xu
CL
Chong-Dao Lu