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

Fabien Hermant; Emmanuel Nicolas; Yvan Six

doi:10.1016/j.tet.2014.04.006

Journal articles

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

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

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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 : Monday, March 9, 2020 - 9:10:05 AM

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

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

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