title: Stereoselective Synthesis of β-Lactam-triflones under Catalyst-Free Conditions.
abstract: The first example of the synthesis of β-lactam-triflones is described. Treatment of 2-diazo-1-aryl-2-(trifluoromethylsulfonyl)ethanones 1c-f with imines 2 under catalyst-free heating conditions provides pharmaceutically attractive multisubstituted β-lactam-triflones 3 in good to high yields with regio- and diastereoselectivities. A successive Wolff rearrangement and Staudinger [2 + 2] cycloaddition reaction are key elements for the success of this transformation.
authors.affiliation: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Zhongyan
authors.initials: Z
authors.lastname: Huang
authors.affiliation: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Chen
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Etsuko
authors.initials: E
authors.lastname: Tokunaga
authors.affiliation: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Sumii
authors.affiliation: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555, Japan.
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
mesh_terms: D061565:Cycloaddition Reaction; D007097:Imines / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007097:Imines; D047090:beta-Lactams