title: Stereodivergent synthesis of beta-lactams using thermal rearrangement of aminocyclobutenones.
abstract: In the present study, the stereodivergent synthesis of both cis- and trans-beta-lactams is presented using the following three reactions: iminocyclobutenone formation, chemoselective reduction of imino groups, and thermal rearrangement of aminocyclobutenones as crucial steps, in which the starting materials, iminocyclobutenones, were readily synthesized using conjugate addition reactions of alkynyl imines with ketene silyl acetals in good yields.
authors: Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
authors: Iwao
authors: I
authors: Hachiya
authors: Takuya
authors: T
authors: Yoshitomi
authors: Yukari
authors: Y
authors: Yamaguchi
authors: Makoto
authors: M
authors: Shimizu
mesh_terms: D000080:Acetals / Q000737:chemistry*; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000080:Acetals; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D047090:beta-Lactams; C008223:ketene