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.
Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors / Sartori, Andrea; Curti, Claudio; Battistini, Lucia; Burreddu, P.; Rassu, G.; Pelosi, Giorgio; Casiraghi, Giovanni; Zanardi, Franca. - In: TETRAHEDRON. - ISSN 0040-4020. - 64:(2008), pp. 11697-11705. [10.1016/j.tet.2008.10.007]
Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors
SARTORI, Andrea;CURTI, Claudio;BATTISTINI, Lucia;PELOSI, Giorgio;CASIRAGHI, Giovanni;ZANARDI, Franca
2008-01-01
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.| File | Dimensione | Formato | |
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