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Direct-type vinylogous Mukaiyama-Michael addition reactions involving pyrrolinone donors

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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DOI: 10.1016/j.tet.2008.10.007

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 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.

Item Type:Article
ID Code:1379
Status:Published
Refereed:Yes
Uncontrolled Keywords:Vinylogous Michael reaction, 1,4-Addition reaction, pyrrolin-2-ones, 4-methoxytetramates
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Pergamon / Elsevier
ISSN:0040-4020
Copyright Holders:© 2008 Elsevier
Additional Information:Pubblicato online il 10 ottobre 2008.
Deposited On:18 Aug 2009 10:05

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