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Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors |
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| Authors: | Andrea Sartori Lucia Battistini Gloria Rassu Giovanni Casiraghi |
| Institution: | a Dipartimento Farmaceutico, Università degli Studi di Parma, Viale G. P. Usberti 27A, Parma I-43100, Italy b Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, Li Punti, Sassari I-07040, Italy c Dipartimento di Chimica Generale ed Inorganica, Chimica Analitica, Chimica Fisica, Università di Parma, Viale G. P. Usberti 17A, I-43100 Parma, Italy |
| Abstract: | The direct Mukaiyama-Michael addition of vinylogous tetramate donors to a number of different Michael acceptors has been easily executed, by employing the TMSOTf/Et3N mixture as soft Lewis acid/base promoter agent. Richly functionalized, highly manipulable γ-substituted pyrrolinone products were practically synthesized in acceptable to excellent yields, and with diastereoselectivities heavily relying upon the substituent at the nitrogen atom of the pyrrolinone donor. |
| Keywords: | Vinylogous Michael reaction 1 4-Addition reaction Pyrrolin-2-ones 4-Methoxytetramates |
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