title: Highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl esters via Sc(OTf)(3)-catalyzed imino Mukaiyama-aldol type reaction of 2,5-bis(trimethylsilyloxy)furan with imines.
abstract: Functionalized gamma-lactams are found to be crucial intermediates in the synthesis of biologically important natural products. We herein described a highly diastereoselective synthesis of beta-carboxy-gamma-lactams and their ethyl ester derivatives, in high yields with high diastereomeric ratio, via the Mukaiyama-aldol type reaction of 2,5-bis(trimethysilyloxy)furan with imines, employing Sc(OTf)(3) as a catalyst.
authors.affiliation: Department of Chemistry, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand. scmpk@mahidol.ac.th
authors.forename: Manat
authors.initials: M
authors.lastname: Pohmakotr
authors.forename: Nattawut
authors.initials: N
authors.lastname: Yotapan
authors.forename: Patoomratana
authors.initials: P
authors.lastname: Tuchinda
authors.forename: Chutima
authors.initials: C
authors.lastname: Kuhakarn
authors.forename: Vichai
authors.initials: V
authors.lastname: Reutrakul
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: C522531:2,5-bis(trimethylsilyloxy)furan; D002264:Carboxylic Acids; D004952:Esters; D005030:Ethylenes; D005663:Furans; D007097:Imines; D007769:Lactams; D008698:Mesylates; D014297:Trimethylsilyl Compounds; C436603:scandium triflate; C036216:ethylene; D012538:Scandium