Chemoenzymatic Synthesis of -Substituted Serines via Enantiodivergent Transformation
نویسندگان
چکیده
A series of (R)-N-Cbz-2-alkyl-2-amino-3-hydroxypropyl acetates was prepared by enzymatic acetylation of NCbz-2-alkyl-2-aminopropane-1,3-diols with immobilized lipoprotein lipase from Pseudomonas sp. in up to 98% enantiomeric excess (ee). Enantiodivergent oxidation of (R)-N-Cbz-2-alkyl-2-amino-3-hydroxypropyl acetates readily furnished (R)and (S)-substituted serines ( -benzylserines and -methylserines). Enzymatic hydrolysis of diethyl N-Cbz-2amino-2-methylmalonate catalyzed by porcine liver esterase afforded (R)-N-Cbz-2-amino-3-ethoxy-2-methyl-3oxopropanoic acid in 97% ee. (R)-N-Cbz-2-amino-3-ethoxy-2-methyl-3-oxopropanoic acid was also transformed to both enantiomers of -methylserine via enantiodivergent reduction.
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