Sartori, Andrea and Curti, Claudio and Battistini, Lucia and Burreddu, Paola and Rassu, Gloria Maria Rita and Pelosi, Giorgio and Casiraghi, Giovanni and Zanardi, Franca (2008) Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors. Tetrahedron, Vol. 64 (51), p. 11697-11705. ISSN 0040-4020. Article.
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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 y-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.
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