Efficient Synthesis of New Fluorinated β-Amino Acid Enantiomers through Lipase-Catalyzed Hydrolysis
Keyword(s):
An efficient and novel enzymatic method has been developed for the synthesis of β-fluorophenyl-substituted β-amino acid enantiomers through lipase PSIM (Burkholderia cepasia) catalyzed hydrolysis of racemic β-amino carboxylic ester hydrochloride salts 3a–e in iPr2O at 45 °C in the presence of Et3N and H2O. Adequate analytical methods were developed for the enantio-separation of racemic β-amino carboxylic ester hydrochlorides 3a–e and β-amino acids 2a–e. Preparative-scale resolutions furnished unreacted amino esters (R)-4a–e and product amino acids (S)-5a–e with excellent ee values (≥99%) and good chemical yields (>48%).
2008 ◽
Vol 19
(17)
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pp. 2072-2077
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2007 ◽
Vol 73
(16)
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pp. 5370-5373
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1956 ◽
Vol 104
(2)
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pp. 183-191
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1925 ◽
Vol 98
(687)
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pp. 58-65
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2007 ◽
Vol 13
(22)
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pp. 6397-6401
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1971 ◽
Vol 24
(4)
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pp. 1235
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