title: BINAPHANE-catalyzed asymmetric synthesis of trans-β-lactams from disubstituted ketenes and N-tosyl arylimines.
abstract: The development of a BINAPHANE-catalyzed formal [2 + 2]-cycloaddition of disubstituted ketenes and inexpensive N-tosyl arylimines that provides access to a variety of highly substituted β-lactams (16 examples) is described. The BINAPHANE catalytic system displays moderate to excellent enantioselectivity (up to 98% ee) and high diastereoselectivity in most cases, favoring formation of the trans-diastereomer (13 examples with dr ≥ 90:10).
authors.affiliation: Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.
authors.forename: Shi
authors.initials: S
authors.lastname: Chen
authors.forename: Eric C
authors.initials: EC
authors.lastname: Salo
authors.forename: Kraig A
authors.initials: KA
authors.lastname: Wheeler
authors.forename: Nessan J
authors.initials: NJ
authors.lastname: Kerrigan
mesh_terms: D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C409582:1,2-bis(4,5-dihydro-3H-dinaphtho(2,1-c-1',2'-e)phosphepino)benzene; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D009281:Naphthalenes; D014105:Tosyl Compounds; D047090:beta-Lactams; C008223:ketene