Naphthylethylamines as chiral auxiliaries in a stereoselective formation of trans-β-lactams via Staudinger cycloaddition

Autor: Aleksandar R. Todorov, Margarita Stoylova-Dicheva, Vanya B. Kurteva
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: ARKIVOC, Vol 2011, Iss 11, Pp 198-212 (2011)
ISSN: 1551-7012
1551-7004
Popis: As a part of our study on the chiral amine induced stereoselectivity in the formation of the trans - azetidin-2-one ring via Staudinger cycloaddition, the efficiency of the enantioisomeric naphthylethylamines as chiral auxiliaries was examined. It was found that the isomeric 1-(2- naphthyl)ethylamines induced commensurable selectivities with those obtained by the corresponding phenylethylamines, good to excellent yields with de up to 48%. In contrast, the 1- (1-naphthyl)ethylamine auxiliaries led to excellent conversion but with dramatic loss of selectivity, with a maximum of 14% de . The �-lactams obtained were screened in vitro against 10 bacteria and 3 fungi but significant antimicrobial activities were not observed.
Databáze: OpenAIRE
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