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.

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]

Triclorosilane-mediated stereoselective synthesis of beta-amino esters and their conversion to highly enantiomerically enriched beta-lactams

S. Guizzetti
;
M. Benaglia
Secondo
;
M. Bonsignore
Penultimo
;
L. Raimondi
Ultimo
2011

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.
catalyzed asymmetric hydrogenation; unnatural alpha-amino; n-aryl imines; reductive amination; enantioselective reduction; organic activators; acid-derivates; aromatic ketones; trichlorosilane; ketimines
Settore CHIM/06 - Chimica Organica
17-nov-2010
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/155896
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