Issue 20, 2008
From the journal:

Organic & Biomolecular Chemistry

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

Eiji Tayama,*a   Kiwako Oriharaa  and  Hiroshi Kimuraa  

* Corresponding authors

a Graduate School of Science and Technology, Niigata University, Japan
E-mail: tayama@gs.niigata-u.ac.jp
Fax: +81 25 262 7741
Tel: +81 25 262 7741

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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Article information

DOI
https://doi.org/10.1039/B811162F
Article type
Paper
Submitted
01 Jul 2008
Accepted
17 Jul 2008
First published
27 Aug 2008

Org. Biomol. Chem., 2008,6, 3673-3680

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

E. Tayama, K. Orihara and H. Kimura, Org. Biomol. Chem., 2008, 6, 3673 DOI: 10.1039/B811162F

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