Stereodivergent synthesis of beta-lactams using thermal rearrangement of aminocyclobutenones.
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.
Hachiya
Iwao
I
Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan.
Yoshitomi
Takuya
T
Yamaguchi
Yukari
Y
Shimizu
Makoto
M
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
D000080:Acetals; D005030:Ethylenes; D007097:Imines; D007659:Ketones; D047090:beta-Lactams; C008223:ketene