Synthesis of Bicyclic Pyroglutamic Acid Featuring the Ugi Reaction and a Unique Stereoisomerization at the Angular Position by Grob Fragmentation Followed by a Transannular Ketene [2+2] Cycloaddition Reaction

Autor:	Kerem Erol Ozboya, Mitchell Vamos, Yoshihisa Kobayashi
Rok vydání:	2007
Předmět:	chemistry.chemical_compound Grob fragmentation chemistry Bicyclic molecule Stereochemistry Organic Chemistry Ketene Ugi reaction Basic hydrolysis Pyroglutamic acid Cycloaddition
Zdroj:	Synlett. 2007:1595-1599
ISSN:	1437-2096 0936-5214
DOI:	10.1055/s-2007-982538
Popis:	A stereoisomerization at the angular position of N-acylindoles during basic hydrolysis was discovered to give only the syn-bicyclic pyroglutamic acid, proceeding through a transannular [2+2] cycloaddition of a ketene-ketone intermediate generated by a Grob fragmentation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::54b557fddcc613bd1264a503f00c99d3 https://doi.org/10.1055/s-2007-982538 Zobrazit plný text záznamu