Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study

Abstract : 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.
Document type :
Journal articles
Complete list of metadatas

https://hal-polytechnique.archives-ouvertes.fr/hal-01015278
Contributor : Denis Roura <>
Submitted on : Thursday, June 26, 2014 - 10:53:45 AM
Last modification on : Wednesday, March 27, 2019 - 4:17:00 PM

Identifiers

Collections

Citation

Fabien Hermant, Emmanuel Nicolas, Yvan Six. Ti-mediated intramolecular cyclopropanation of N-alkenyl thioamides: scope and mechanistic study. Tetrahedron, Elsevier, 2014, 70 (25), pp.3924-3930. ⟨10.1016/j.tet.2014.04.006⟩. ⟨hal-01015278⟩

Share

Metrics

Record views

203