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Thiourea derivatives of Tröger's base: Synthesis, enantioseparation and evaluation in organocatalysis of Michael addition to nitroolefins

par Didier, Delphine ;Sergueev, Serguei
Référence Arkivoc, 2009, 14, page (124-134)
Publication Publié, 2009

Article révisé par les pairs

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Résumé :

The catalytic activity of racemic thiourea derivatives of Tröger's base (±)-2-4 in Michael additions of malonate derivatives to trans-β-nitrostyrene was studied. Due to the low basicity of Tröger's base, the outcome of the addition reactions was strongly dependent on the pKa of the nucleophile. Thiourea catalysts (±)-2, 3 were resolved on the chiral stationary phase Whelk O1. Unfortunately, enantiopure catalysts 2 and 3 showed no stereoselectivity in the Michael addition. © ARKAT USA, Inc.