Lipase-Catalyzed Enantioselective Acetylation of Prochiral N-Cbz-2-Alkyl-2-Amino-1,3-Propanediols and Enantiodivergent Synthesis of α-Benzylserine

Title: Lipase-Catalyzed Enantioselective Acetylation of Prochiral N-Cbz-2-Alkyl-2-Amino-1,3-Propanediols and Enantiodivergent Synthesis of α-Benzylserine

Volume: 3 Issue: 10

Author(s): Shigeki Sano, Michiyasu Nakao, Masanori Takeyasu, Takashi Honjo and Yoshimitsu Nagao

Affiliation:

Keywords: Asymmetric synthesis, lipoprotein lipase, acetylation, 1,3-propanediols, enantiodivergent, α-benzylserine

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.

Cite this article as:

Sano Shigeki, Nakao Michiyasu, Takeyasu Masanori, Honjo Takashi and Nagao Yoshimitsu, Lipase-Catalyzed Enantioselective Acetylation of Prochiral N-Cbz-2-Alkyl-2-Amino-1,3-Propanediols and Enantiodivergent Synthesis of α-Benzylserine, Letters in Organic Chemistry 2006; 3 (10) . https://dx.doi.org/10.2174/157017806779025924