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Stereocontrolled Synthesis of Amino‐Substituted Carbocycles by Pd‐Catalyzed Alkene Carboamination Reactions
Author(s) -
White Derick R.,
Wolfe John P.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700466
Subject(s) - alkene , chemistry , nucleophile , catalysis , stereoselectivity , amine gas treating , ligand (biochemistry) , intermolecular force , substrate (aquarium) , organic chemistry , medicinal chemistry , combinatorial chemistry , molecule , biochemistry , oceanography , receptor , geology
Amino‐substituted alkylidenecyclopentanes were synthesized through a stereoselective intermolecular Pd‐catalyzed alkene carboamination reaction between alkenyl triflates bearing a pendant alkene and exogenous amine nucleophiles. The reactions are effective with a range of different substrate combinations, and proceed with generally high diastereoselectivity. Use of ( S )‐ t BuPhox as the ligand in reactions of achiral substrates provides enantioenriched products with up to 98.5:1.5 e.r.
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