Synthesis and enantioselective rearrangement of (Z)-4-triphenylmethoxy-2,3- epoxybutan-1-ol enantiomers

F. Faigl, Angelika Thurner, Ferenc Farkas, Melinda Battancs, L. Poppe

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Efficient enzyme catalyzed kinetic resolutions of a synthetically useful chiral building block, (Z)-4-triphenylmethoxy-2,3-epoxybutan-1-ol, are reported. The highest selectivities were achieved by Lipozyme TL IM and Amano Lipase PS enzymes in the presence of vinyl acetate. Enantiomeric enrichment of the optically active acetate isomer was accomplished by selective crystallization of the racemic part of the enantiomeric mixture. Enzyme catalyzed hydrolysis of the acetate also provided an optically pure epoxybutanol derivative. O-Benzylation of (+)-(Z)-1-hydroxy-4-triphenylmethoxy-2,3-epoxybutane followed by super base promoted diastereo- and enantio-selective rearrangement resulted in (+)-(2R,3R,1′R)-3-[1-hydroxy-2-(triphenylmethoxy)ethyl]-2-phenyloxetane in >98% ee and de. Configurations of the new optically active products were determined by chemical correlation.

Original languageEnglish
Pages (from-to)197-202
Number of pages6
JournalChirality
Volume19
Issue number3
DOIs
Publication statusPublished - 2007

Fingerprint

Enantiomers
Acetates
Enzymes
Enzyme kinetics
Lipases
Crystallization
Lipase
Isomers
Hydrolysis
Derivatives
2,3-epoxybutane
vinyl acetate
Lipozyme

Keywords

  • Chiral oxetane
  • Enantioselective rearrangement
  • Enzymatic resolution
  • Optically active oxirane
  • Organometallic reagents
  • Superbases

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis and enantioselective rearrangement of (Z)-4-triphenylmethoxy-2,3- epoxybutan-1-ol enantiomers. / Faigl, F.; Thurner, Angelika; Farkas, Ferenc; Battancs, Melinda; Poppe, L.

In: Chirality, Vol. 19, No. 3, 2007, p. 197-202.

Research output: Contribution to journalArticle

Faigl, F. ; Thurner, Angelika ; Farkas, Ferenc ; Battancs, Melinda ; Poppe, L. / Synthesis and enantioselective rearrangement of (Z)-4-triphenylmethoxy-2,3- epoxybutan-1-ol enantiomers. In: Chirality. 2007 ; Vol. 19, No. 3. pp. 197-202.
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