Chemoenzymatic Synthesis of Chiral 1-Benzyl-5-(hydroxymethyl)- 2-piperidone Enabled by Lipase AK-Mediated Desymmetrization of Prochiral 1,3-Diol and Its Diacetate

Duc Thinh Khong, Varsha Siri Pamarthy, Timothy Gallagher, Zaher M A Judeh

Research output: Contribution to journalArticle (Academic Journal)peer-review

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Abstract

The synthesis of (R)-1-benzyl-5-(hydroxymethyl)-2-piperidone (1) from key synthon monoacetate (R)-3 has been accomplished conveniently in 6 steps with 93 % ee and in 44 % overall yield. The key step involved lipase AK-mediated desymmetrization of diol 4 to produce monoacetate (R)-3 in 93 % ee and 93 % yield. Additionally, lipase AK-mediated desymmetrization of diacetate 5 readily provided access to monoacetate (S)-3 in 93 % ee and 54 % yield.
Original languageEnglish
Pages (from-to)3084-3089
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number18
Early online date13 Jun 2016
DOIs
Publication statusPublished - Jun 2016

Keywords

  • Enzyme catalysis
  • Enantioselectivity
  • Acylation
  • Nitrogen heterocycles

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