Synthesis and Aldol Stereoselectivity of 2-Oxazolidinones Derived from L-Histidine

Autor:	Francisco Bermejo Gonzalez, Julia Perez Baz, Fernando Mayor Real, Fabio Santinelli
Rok vydání:	1991
Předmět:	Benzaldehyde Steric effects chemistry.chemical_compound chemistry Aldol reaction Stereochemistry Cationic polymerization Substituent Stereoselectivity Aldol condensation General Chemistry Borane Medicinal chemistry
Zdroj:	Scopus-Elsevier
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.64.674
Popis:	The regiospecific synthesis of the 2-oxazolidinones 5b, 7, 12a, and 12b starting from L-histidine la is described. The stereoselectivity in the dibutyl(trifluoromethylsulfonyloxy)borane promoted aldol condensation between the chiral imides 13a and 13b and benzaldehyde was also studied. The formation of a cationic imidazole–boron complex, 14a, occurs before the aldol condensation between 13a and benzaldehyde takes place. However, the condensation between 13b and benzaldehyde occurs without the formation of any boron complex. The steric hindrance of the substituent at C-4 may account for this difference in behavior.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a514dbe85a1dd5221077cd573aa8d280 https://doi.org/10.1246/bcsj.64.674 Zobrazit plný text záznamu