Triclorosilane-mediated stereoselective synthesis of beta-amino esters and their conversion to highly enantiomerically enriched beta-lactams
Articolo
Data di Pubblicazione:
2011
Citazione:
Triclorosilane-mediated stereoselective synthesis of beta-amino esters and their conversion to highly enantiomerically enriched beta-lactams / S. Guizzetti, M. Benaglia, M. Bonsignore, L. Raimondi. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 9:3(2011), pp. 739-743. [10.1039/c0ob00570c]
Abstract:
A highly stereoselective trichlorosilane-mediated reduction of N-benzyl enamines was developed; the combination of a low cost, easy to make metal-free catalyst and an inexpensive chiral auxiliary allowed to perform the reaction on substrates with different structural features often with total control of the stereoselectivity. By easy deprotection through hydrogenolysis followed by conversion of β-aminoester to 2-azetidinones, the synthesis of enantiomerically pure β-lactams (>98% e.e.) was successfully accomplished.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
catalyzed asymmetric hydrogenation; unnatural alpha-amino; n-aryl imines; reductive amination; enantioselective reduction; organic activators; acid-derivates; aromatic ketones; trichlorosilane; ketimines
Elenco autori:
S. Guizzetti, M. Benaglia, M. Bonsignore, L. Raimondi
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