New synthetic routes to optically active α-quaternary α-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet–Hauser rearrangements?

Organic & Biomolecular Chemistry Pub Date: 2008-08-27 DOI: 10.1039/B811162F

Abstract

The Stevens rearrangement of N-allylic α-aryl amino acid-derived ammonium salts and the Sommelet–Hauser rearrangement of N-benzylic α-alkyl amino acid-derived ammonium salts are shown to proceed with remarkably high levels of diastereoselectivity. The methods presented in this work provide new routes to optically active α-quaternary α-aryl amino acid derivatives.

Graphical abstract: New synthetic routes to optically active α-quaternary α-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet–Hauser rearrangements
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