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β‐Amino Propargylic Fluorides through Stereoselective Electrophilic Fluorodesilylation of 4‐Amino‐1‐allenylsilanes
Author(s) -
Bochatay Valentin N.,
Chemla Fabrice,
Ferreira Franck,
Jackowski Olivier,
PerezLuna Alejandro
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800862
Subject(s) - selectfluor , stereoselectivity , chemistry , electrophile , electrophilic fluorination , conformational isomerism , amino acid , stereochemistry , electrophilic addition , organic chemistry , catalysis , molecule , biochemistry
Herein, we present the stereoselective synthesis of anti ‐β‐amino propargylic fluorides through the anti ‐S E 2′ electrophilic fluorodesilylation reaction of 4‐amino‐1‐allenylsilanes with Selectfluor®. The stereoselectivity of the reaction was explained by a preferred N ‐inside conformer.
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