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Zirconium‐Catalyzed Ethylmagnesiation of Imines − Scope and Mechanism
Author(s) -
Gandon Vincent,
Bertus Philippe,
Szymoniak Jan
Publication year - 2001
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 - 10.1002/1099-0690(200110)2001:19<3677::aid-ejoc3677>3.0.co;2-1
Subject(s) - chemistry , aldimine , zirconium , catalysis , reagent , hydrolysis , alkyl , organic chemistry , reaction mechanism , inert , combinatorial chemistry , medicinal chemistry
The title reaction has been developed for a series of aldimines and ketimines. Most notably, ketimines − which are totally inert towards alkyl Grignard reagents in the absence of the zirconium catalyst − react smoothly when 10 mol % of Cp 2 ZrCl 2 is added. The mechanism of the reaction has been studied. The intermediate azazirconacycle proved to react by two competing pathways involving mono‐ and dimagnesiated final products before hydrolysis.