D. Ach, V. Reboul, P. Metzner
Sep 1, 2003
Citations
0
Influential Citations
10
Citations
Journal
European Journal of Organic Chemistry
Abstract
N,N-Dialkyl-2-methylbenzenecarbothioamides and naphthalenecarbothioamides were prepared by thionation of amides with Lawesson’s reagent under unusual conditions. Their axial chirality was evidenced. Benzylic deprotonation of thioamides bearing N,N-diisopropyl groups with sec-butyllithium was selective. The resulting anions were reacted with prochiral electrophiles (aromatic aldehydes, an unsaturated aldehyde or ketone, and an imine) to afford diastereomeric adducts (up to 88:12 dr). This is the first report on atroposelective C−C bond formation in the benzylic position of thioamides. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)