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Chemo‐ and Regioselective Preparation and Reaction of a Kinetic Zinc Enolate Formed from a Thiol Ester and Bis(iodozincio)methane
Author(s) -
Ikeda Zenichi,
Hirayama Takaharu,
Matsubara Seijiro
Publication year - 2006
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.200602950
Subject(s) - electrophile , regioselectivity , zinc , chemistry , thiol , catalysis , methane , organic chemistry , polymer chemistry
Reactive functionalized enolates that are otherwise difficult to obtain can be prepared in a simple procedure by the treatment of a thiol ester with bis(iodozincio)methane in the presence of a palladium catalyst (see scheme). The terminal zinc enolates thus formed are kinetically controlled and react with a variety of electrophiles, such as aldehydes, ketones, and acyl cyanides. FG=functional group.