title: Recent Advances in the Base-Induced Sommelet-Hauser Rearrangement of Amino Acid Derived Ammonium Ylides.
abstract: The Sommelet-Hauser rearrangement of N-benzylic ammonium ylides generated from ammonium salts is an interesting and useful transformation that enables one to convert a readily accessible C-N bond into a new C-C bond to an aromatic ring. The rearrangement was discovered by Sommelet in 1937, studied in detail by Hauser, and applied to organic synthesis by Sato until 1999. Further studies have not advanced because several competitive side reactions and structural limitations of the products severely limit the substrate scope and synthetic applications. In this Personal Account, a history of the research in problem solving and recent advances in the base-induced Sommelet-Hauser rearrangement are described. This synthetic method developed by my group provides efficient access to various types of α-aryl-α-amino acid and α-aryl-β-amino acid derivatives.
authors.affiliation: Department of Chemistry, Faculty of Science, Niigata University, 2-8050 Ikarashi, Nishi-ku, Niigata, 950-2181, Japan.
authors.forename: Eiji
authors.initials: E
authors.lastname: Tayama
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D064751:Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods; D008958:Models, Molecular; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D064751:Ammonium Compounds; D001597:Benzylidene Compounds; D012492:Salts
keywords: amino acids, ammonium salts, ammonium ylides, rearrangement, synthetic methods