Highly regio- and enantioselective reduction of 1-chloro-2,4-alkanediones using baker's yeast: Effects of organic solvents as additives

Jing Nan Cui, Ryoji Teraoka, Tadashi Ema, Takashi Sakai, Masanori Utaka

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Bakers' yeast reduction of 1-chloro-2,4-alkanediones 1a afforded 1-chloro-2-hydroxy-4-alkanones 2a regioselectively with low optical purities. Application of inhibitors and heat-treatment of bakers' yeast enhanced the optical purities toward the S enantiomer (88-91% ee). Organic solvents added in small amounts were also found to enhance the S selectivity significantly. High optical purities 94-96% ee were achieved by the combined action of the inhibitor, heat-treatment, and organic solvent.

Original languageEnglish
Pages (from-to)3021-3024
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number17
DOIs
Publication statusPublished - Apr 28 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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