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Issue 3, 2011
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Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams

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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.

Graphical abstract: Triclorosilane-mediated stereoselective synthesis of β-amino esters and their conversion to highly enantiomerically enriched β-lactams

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Article information


Submitted
12 Aug 2010
Accepted
05 Oct 2010
First published
17 Nov 2010

Org. Biomol. Chem., 2011,9, 739-743
Article type
Paper

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

S. Guizzetti, M. Benaglia, M. Bonsignore and L. Raimondi, Org. Biomol. Chem., 2011, 9, 739
DOI: 10.1039/C0OB00570C

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