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.

Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates / Sartori, Andrea; Dell'Amico, L.; Curti, Claudio; Battistini, Lucia; Pelosi, Giorgio; Rassu, G.; Casiraghi, Giovanni; Zanardi, Franca. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 353:(2011), pp. 3278-3284. [10.1002/adsc.201100572]

Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates

SARTORI, Andrea;CURTI, Claudio;BATTISTINI, Lucia;PELOSI, Giorgio;CASIRAGHI, Giovanni;ZANARDI, Franca
2011-01-01

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.
2011
Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates / Sartori, Andrea; Dell'Amico, L.; Curti, Claudio; Battistini, Lucia; Pelosi, Giorgio; Rassu, G.; Casiraghi, Giovanni; Zanardi, Franca. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 353:(2011), pp. 3278-3284. [10.1002/adsc.201100572]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2376313
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