Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: Scope and mechanistic study
Although thioamides generally undergo a reductive alkylation process when they are treated with a Grignard reagent in the presence of Ti(OiPr) 4, substrates fitted with a but-3-enyl substitution at the nitrogen atom are shown to be converted into bicyclic aminocyclopropanes. These reactions are compared with the similar cyclisations of the corresponding carboxylic amide substrates. A mechanistic study is provided. Coincidently, new reagent systems are identified for the mediation of the same transformation.
Hermant, Fabien,Nicolas, Emmanuel,Six, Yvan
supporting information
p. 3924 - 3930
(2014/06/09)
Studies on the intramolecular Kulinkovich-de Meijere reaction of disubstituted alkenes bearing carboxylic amide groups
The intramolecular Kulinkovic-de Meijere cylcopropanation of some distributed alkenes bearing amide groups was studied. These reactions proved to be moderately efficient but highly distereoselective: single diastereoisomers were obtained from diastereoiso
Ouhamou, Nouara,Six, Yvan
p. 3007 - 3009
(2007/10/03)
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