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Gram‐Scale Synthesis of Amines Bearing a gem ‐Difluorocyclopropane Moiety
Author(s) -
Nosik Pavel S.,
Gerasov Andrii O.,
Boiko Rodion O.,
Rusanov Eduard,
Ryabukhin Sergey V.,
Grygorenko Oleksandr O.,
Volochnyuk Dmitriy M.
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700857
Subject(s) - chemistry , moiety , reactivity (psychology) , reagent , trifluoromethyl , substrate (aquarium) , bicyclic molecule , iodide , methyl iodide , sodium iodide , silane , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , medicine , alkyl , alternative medicine , oceanography , pathology , geology
The synthesis of monocyclic, spirocyclic and fused bicyclic secondary amines bearing a gem ‐difluorocyclopropane moiety via difluorocyclopropanation of unsaturated N ‐Boc derivatives using the trifluoromethyl(trimethyl)silane/sodium iodide [CF 3 SiMe 3 ‐NaI] system is described. The relative order of the substrate reactivity is established. It is shown that for the reactive alkenes the standard reaction conditions can be used, whereas for the substrates with low reactivity, slow addition of the Ruppert–Prakash reagent is necessary.