Application of samarium diiodide (SmI2)-induced reduction of gamma-acetoxy-alpha,beta-enoates with alpha-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives.
Gamma-acetoxy-alpha,beta-enoates were easily reduced by samarium diiodide (SmI2) in THF to generate samarium dienolates which were kinetically trapped with ease at their alpha-positions by electrophiles (proton, aldehydes or ketones) to yield (E)-alkene dipeptide isosteres or gamma-amino acid derivatives in high chemical yields.
Otaka
Akira
A
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. aotaka@pharm.kyoto-u.ac.jp
Yukimasa
Akira
A
Watanabe
Junko
J
Sasaki
Yoshikazu
Y
Oishi
Sinya
S
Tamamura
Hirokazu
H
Fujii
Nobutaka
N
D000085:Acetates / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; D000596:Amino Acids; D007454:Iodides; D009942:Organometallic Compounds; D012493:Samarium; C409809:samarium diiodide