Aqueous and Solvent-Free Uncatalyzed Three-Component Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates
Articolo
Data di Pubblicazione:
2011
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 g-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.
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 g-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.
Tipologia CRIS:
01.01 Articolo in rivista
Keywords:
catalyst-free conditions; green chemistr; Mukaiyama-Mannich reactio; synthetic methods
Elenco autori:
Rassu, GLORIA MARIA RITA
Link alla scheda completa:
Pubblicato in: