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

DOI: 10.1016/S0040-4039(98)01123-X

Source and publish data:

Tetrahedron Letters p. 5571 - 5574 (1998)

Update date:2022-09-26

Topics:

Authors:

Sano, Shigeki

Hayashi, Kazuhiko

Miwa, Toshio

Ishii, Takahiro

Fujii, Michiho

Mima, Hiromi

Nagao, Yoshimitsu

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Article abstract of DOI:10.1016/S0040-4039(98)01123-X

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

Full text of DOI:10.1016/S0040-4039(98)01123-X

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