Tetramic acids and derivatives by telluride-triggered Dieckmann cyclizations

Autor: Matthew Purzycki, Venkata Subbarao Kandula, Matthew W. Bacler, Elliot Hohn, Dmitry V. Avilov, Donald C. Dittmer, Zachary J. Martens
Rok vydání: 2009
Předmět:
Zdroj: ARKIVOC, Vol 2010, Iss 6, Pp 61-83 (2009)
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0011.608
Popis: Treatment of alpha-bromoacyl amides of esters of N-protected alpha-amino acids with lithium telluride yields an amide enolate which cyclizes to unstable tetramic acids (2, 4-pyrrolidinediones) which can be converted to stable derivatives (e.g. enol esters, silyl enol ethers, enol tosylates). Reaction conditions are modified to reduce unwanted side reactions: protonation of the enolate, self-catalyzed intermolecular aldol rections of the tetramic acids, and potential racemization at the alpha-carbon atom of the amino acid.
Databáze: OpenAIRE