New synthetic routes to optically active alpha-quaternary alpha-aryl amino acid derivatives via the diastereoselective Stevens and Sommelet-Hauser rearrangements.
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.
Tayama
Eiji
E
Graduate School of Science and Technology, Niigata University, Niigata 950-2181, Japan. tayama@gs.niigata-u.ac.jp
Orihara
Kiwako
K
Kimura
Hiroshi
H
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000440:Butanols / Q000737:chemistry; D055095:Optics and Photonics; D013237:Stereoisomerism; D013379:Substrate Specificity
D000596:Amino Acids; D000440:Butanols; C077664:tert-butoxide, potassium