Tin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement.
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
Bandyopadhyay
Anupam
A
Department of Chemistry, Indian Institute of Science Education and Research, Garware Circle, Pashan, Pune, 411021, India.
Agrawal
Neha
N
Mali
Sachitanand M
SM
Jadhav
Sandip V
SV
Gopi
Hosahudya N
HN
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000737:chemistry*; D003979:Diazonium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D017971:Tin Compounds / Q000737:chemistry*
D000447:Aldehydes; D000596:Amino Acids; D053138:Cyclohexenes; D003979:Diazonium Compounds; D004952:Esters; D017971:Tin Compounds; C519041:semipinacol; C023599:stannous chloride; C032111:diazoacetic ester