Title of article :
Lipase-Catalyzed Enantioselective Acetylation of Prochiral N-Cbz-2-Alkyl-2-Amino-1,3-Propanediols and Enantiodivergent Synthesis of -Benzylserine
Author/Authors :
Sano, Shigeki The University of Tokushima - School of Pharmaceutical Sciences, Japan , Nakao, Michiyasu The University of Tokushima - School of Pharmaceutical Sciences, Japan , Takeyasu, Masanori The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Honjo, Takashi The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan , Nagao, Yoshimitsu The University of Tokushima - Graduate School of Pharmaceutical Sciences, Japan
Abstract :
Enzymatic acetylation of several varieties of N-Cbz-2-alkyl-2-amino-1,3-propanediols 3a-d with immobilized lipoprotein lipase from Pseudomonas sp. afforded N-Cbz-3-acetoxy-2-alkyl-2-amino-1-propanols 4a-d in up to 98% ee. A facile synthesis of (R)- and (S)-a-benzylserines [(R)- and (S)-8a] was achieved by enantiodivergent conversion of chiral N-Cbz-3-acetoxy-2-amino-2-benzyl-1-propanol (R)-4a.
Keywords :
Asymmetric synthesis , lipoprotein lipase , acetylation , 1 , 3 , propanediols , enantiodivergent , a , benzylserine
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
