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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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.
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