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

作者:Sartori Andrea*; Dell'Amico Luca; Curti Claudio; Battistini Lucia; Pelosi Giorgio; Rassu Gloria; Casiraghi Giovanni; Zanardi Franca
来源:Advanced Synthesis & Catalysis, 2011, 353(18): 3278-3284.
DOI:10.1002/adsc.201100572

摘要

A catalyst-free, environmentally benign three-component vinylogous MukaiyamaMannich 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 ?-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.

  • 出版日期2011-12