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Intramolecular “Hydroiminiumation” of Alkenes: Application to the Synthesis of Conjugate Acids of Cyclic Alkyl Amino Carbenes (CAACs)
Author(s) -
Jazzar Rodolphe,
Dewhurst Rian D.,
Bourg JeanBaptiste,
Donnadieu Bruno,
Canac Yves,
Bertrand Guy
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200605083
Subject(s) - hydroamination , intramolecular force , iminium , chemistry , nucleophile , stereocenter , alkyl , conjugate , intramolecular reaction , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , mathematical analysis , mathematics
A rival for the hydroamination reaction : The intramolecular “hydroiminiumation” reaction features some distinct advantages over intramolecular hydroamination since the resulting prochiral iminium ions potentially allow the subsequent addition of a large range of nucleophiles to afford a new stereogenic center α to the nitrogen atom (see scheme; Nu − =nucleophile).