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.
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.
Pohmakotr
Manat
M
Department of Chemistry, Mahidol University, Rama 6 Road, Bangkok 10400, Thailand. scmpk@mahidol.ac.th
Yotapan
Nattawut
N
Tuchinda
Patoomratana
P
Kuhakarn
Chutima
C
Reutrakul
Vichai
V
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*
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