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Aqueous and Solvent‐Free Uncatalyzed Three‐Component Vinylogous Mukaiyama–Mannich Reactions of Pyrrole‐Based Silyl Dienolates
Author(s) -
Sartori Andrea,
Dell'Amico Luca,
Curti Claudio,
Battistini Lucia,
Pelosi Giorgio,
Rassu Gloria,
Casiraghi Giovanni,
Zanardi Franca
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100572
Subject(s) - chemistry , silylation , aldehyde , vicinal , aqueous solution , pyrrole , catalysis , solvent , organic chemistry , mannich reaction , selectivity , combinatorial chemistry
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.