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

2011 ARKIVOC  
As a part of our study on the chiral amine induced stereoselectivity in the formation of the transazetidin-2-one ring via Staudinger cycloaddition, the efficiency of the enantioisomeric naphthylethylamines as chiral auxiliaries was examined. It was found that the isomeric 1-(2naphthyl)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
more » ... xcellent conversion but with dramatic loss of selectivity, with a maximum of 14% de. The β-lactams obtained were screened in vitro against 10 bacteria and 3 fungi but significant antimicrobial activities were not observed.
doi:10.3998/ark.5550190.0012.b18 fatcat:6vrcf2ocpfabrihvxffbs4wa44