Lipase/Oxovanadium Co-Catalyzed Dynamic Kinetic Resolution of Propargyl Alcohols: Competition between Racemization and Rearrangement

Shinji Kawanishi, Shinya Oki, Dhiman Kundu, Shuji Akai

Research output: Contribution to journalArticle

Abstract

Quantitative conversion of racemic propargyl alcohols into optically active propargyl esters with up to 99% ee has been achieved by lipase/oxovanadium co-catalyzed dynamic kinetic resolution, which combines the lipase-catalyzed enantioselective esterification of the racemic substrates and the in situ racemization of the remaining enantiomers. The success is owed to our discovery of a magic solvent, (trifluoromethyl)benzene, that accelerated the racemization while sufficiently suppressing the common oxovanadium-catalyzed rearrangement of propargyl alcohols to irreversibly produce enals.

Original languageEnglish
Pages (from-to)2978-2982
Number of pages5
JournalOrganic Letters
Volume21
Issue number9
DOIs
Publication statusPublished - May 3 2019

Fingerprint

Lipase
alcohols
Magic
Kinetics
Enantiomers
Esterification
enantiomers
kinetics
Benzene
esters
Esters
benzene
Substrates
propargyl alcohol

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lipase/Oxovanadium Co-Catalyzed Dynamic Kinetic Resolution of Propargyl Alcohols : Competition between Racemization and Rearrangement. / Kawanishi, Shinji; Oki, Shinya; Kundu, Dhiman; Akai, Shuji.

In: Organic Letters, Vol. 21, No. 9, 03.05.2019, p. 2978-2982.

Research output: Contribution to journalArticle

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