New enantiodivergent procedure for the syntheses of chiral α-substituted serines from α-alkyl-α-aminomalonates utilizing enzymatic hydrolysis

✍ Scribed by Shigeki Sano; Kazuhiko Hayashi; Toshio Miwa; Takahiro Ishii; Michiho Fujii; Hiromi Mima; Yoshimitsu Nagao

• Book ID: 104259583
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 219 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01123-x

✦ Synopsis

Porcine liver esterase (PLE)-or rabbit liver esterase (RLE)-catalyzed hydrolysis of the pro-S ester group of diethyl cc-alkyi-~-(benzyloxycarbonylamino)malonates 2a-c afforded (R)-ethyl 0t-alkyl-et -(benzyloxycarbonylamino)malonates 3a-c each in excellent enantiomeric excess. Enantiodivergent reductions of these acid esters 3a-c readily furnished both the corresponding enantiomeric m-substituted serines (R)-and (S)-5a-¢.