Anodic modification of proline derivatives using a lithium perchlorate/nitromethane electrolyte solution.
[reaction: see text] N-Acyliminium cation of prolines was efficiently generated to accumulate in an undivided cell at 0 degrees C by an anodic oxidation of N-acylprolines or alpha'-phenylsulfanylated N-acylproline derivatives in a lithium perchlorate/nitromethane solution. The iminium cation intermediates gave modified prolines by a reaction with nucleophiles under mild conditions.
Kim
Shokaku
S
Laboratory of Bio-organic Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
Hayashi
Kanako
K
Kitano
Yoshikazu
Y
Tada
Masahiro
M
Chiba
Kazuhiro
K
D004566:Electrodes; D004573:Electrolytes / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry*; D009595:Nitroparaffins / Q000737:chemistry*; D010472:Perchlorates / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D012996:Solutions
D004573:Electrolytes; D018020:Lithium Compounds; D009595:Nitroparaffins; D010472:Perchlorates; D012996:Solutions; D011392:Proline; D008697:Methane; C054684:lithium perchlorate; C008640:nitromethane