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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 10 , 2006

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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, α-benzylserine

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Article Details

VOLUME: 3
ISSUE: 10
Year: 2006
Page: [764 - 767]
Pages: 4
DOI: 10.2174/157017806779025924
Price: $58

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