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

Fabien Hermant 1 Emmanuel Nicolas 2 Yvan Six 1, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
2 LCM - Laboratoire de chimie moléculaire
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.
Keywords : Kulinkovich-type reactions Thioamides Aminocyclopropanes Grignard reagents Diastereoselectivity
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https://hal-polytechnique.archives-ouvertes.fr/hal-01015278
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Submitted on : Thursday, June 26, 2014 - 10:53:45 AM
Last modification on : Wednesday, April 7, 2021 - 10:14:02 AM

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CNRS | X-DCSO | X-LCM | X | PARISTECH | INC-CNRS | X-DEP-CHIM

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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⟩

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