MilliporeSigma
  • Home
  • Search Results
  • New synthetic routes to optically active alpha-quaternary alpha-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet-Hauser rearrangements.

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

Organic & biomolecular chemistry (2008-10-10)
Eiji Tayama, Kiwako Orihara, Hiroshi Kimura
ABSTRACT

The Stevens rearrangement of N-allylic alpha-aryl amino acid-derived ammonium salts and the Sommelet-Hauser rearrangement of N-benzylic alpha-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 alpha-quaternary alpha-aryl amino acid derivatives.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Potassium tert-butoxide solution, 1.0 M in THF
Sigma-Aldrich
Potassium tert-butoxide, sublimed grade, 99.99% trace metals basis
Sigma-Aldrich
Potassium tert-butoxide, reagent grade, ≥98%