Nucleophilic ring-opening of epoxide and aziridine acetates for the stereodivergent synthesis of β-hydroxy and β-amino γ-lactams.

A highly regio- and stereoselective synthesis of novel β,γ-disubstituted γ-lactams with either an anti or syn relative configuration was developed from readily available epoxide and aziridine acetates. The key steps include the regio- and diastereocontrolled nucleophilic ring-opening of these three-membered heterocycles followed by mild reductive cyclization of the γ-azido ester intermediate. The method was also extended to an asymmetric synthesis of (4R,5S)-4-hydroxy-5-phenylpyrrolidin-2-one from a chiral epoxide acetate. The main features of this versatile synthesis of functionalized γ-lactams include the involvement of inexpensive reagents and mild conditions together with high chemical efficiency.

Citation

Tula B Bisol, Adailton J Bortoluzzi, Marcus M Sá. Nucleophilic ring-opening of epoxide and aziridine acetates for the stereodivergent synthesis of β-hydroxy and β-amino γ-lactams. The Journal of organic chemistry. 2011 Feb 4;76(3):948-62

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PMID: 21194209

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