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Aqueous and solvent-free uncatalyzed three-component vinylogous Mukaiyama–Mannich reactions of pyrrole-based silyl dienolates

Sartori, Andrea and Dell'Amico, Luca and Curti, Claudio and Battistini, Lucia and Pelosi, Giorgio and Rassu, Gloria Maria Rita and Casiraghi, Giovanni and Zanardi, Franca (2011) Aqueous and solvent-free uncatalyzed three-component vinylogous Mukaiyama–Mannich reactions of pyrrole-based silyl dienolates. Advanced Synthesis & Catalysis, Vol. 353 (18), p. 3278-3284. eISSN 1615-4169. Article.

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DOI: 10.1002/adsc.201100572

Abstract

A catalyst-free, environmentally benign three-component vinylogous Mukaiyama–Mannich reaction of pyrrole-based silyl dienolates is presented, which works effectively in both aqueous and solvent-free environments. Both lipophilic and hydrophilic aldehyde candidates are suitable substrates, allowing access to a rich repertoire of unsaturated vicinal aminolactam structures with virtually complete γ-site selectivity and moderate to good anti-diastereoselectivity. The utility of this technology is highlighted by protecting group-free synthesis of densely hydroxylated, sugar-related lactam frameworks. The role of water as an indispensable H-bonding reaction propeller is demonstrated.

Item Type:Article
ID Code:6921
Status:Published
Refereed:Yes
Uncontrolled Keywords:Catalyst-free conditions, green chemistry, Mukaiyama–Mannich reaction, synthetic methods, vinylogy, water
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Blackwell / Wiley
eISSN:1615-4169
Deposited On:03 Jan 2012 13:49

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