Stereoselective Cycloaddition of Monosubstituted Ketene to a Methyl Glyoxylate- and Threonine-Derived Imine: Synthesis of Optically Pure β-Lactamic α-Amino Ester with High Functionality

Autor:	Serge Mignani, Lucien Stella, Isabelle Le Roy, Dominique Mouysset
Rok vydání:	2000
Předmět:	chemistry.chemical_compound chemistry Yield (chemistry) Organic Chemistry Imine Glyoxylate cycle Ketene Stereoselectivity Chloroacetyl chloride Triethylamine Medicinal chemistry Cycloaddition
Zdroj:	Synthetic Communications. 30:3685-3691
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397910008086995
Popis:	The reaction of chloroacetyl chloride and triethylamine with a chiral imine derived from the combination of methyl glyoxylate and protected L-threonine gave two optically active α-amino acid derivatives with a cis-substituted β-lactam skeleton in a 72:28 ratio. The major product is obtained in 59% yield by simple crystallisation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0747216160f4ef66f18cb3b07e61e7e0 https://doi.org/10.1080/00397910008086995 Zobrazit plný text záznamu