Enzymatic reactions for the preparation of homocalycotomine enantiomers

László Schönstein, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Homocalycotomine enantiomers (R)-4 and (S)-4 were prepared by the Candida antarctica lipase B (CAL-B)-catalysed asymmetric O-acylation of N-Boc-protected 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanol (±)-1. The preliminary small-scale experiments were performed either in a continuous-flow system or as batch reactions, while the preparative-scale resolution was carried out in two steps with vinyl acetate as the acyl donor in the presence of Et3N and Na2SO4 in toluene at 3 C, as a batch reaction. Treatment of the resulting amino alcohol (S)-1 and amino ester (R)-3 (ee ≥94%) with 18% HCl, and then with 5 M NaOH, furnished the desired (R)-4 and (S)-4 without a decrease in the enantiomeric excess (ee ≥94%).

Original languageEnglish
Pages (from-to)1059-1062
Number of pages4
JournalTetrahedron Asymmetry
Volume24
Issue number18
DOIs
Publication statusPublished - Sep 30 2013

Fingerprint

Amino alcohols
Amino Alcohols
Acylation
Enantiomers
Candida
enantiomers
Lipases
Toluene
Esters
Ethanol
acylation
preparation
Antarctic regions
toluene
esters
acetates
alcohols
ethyl alcohol
Experiments
heliamine

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Enzymatic reactions for the preparation of homocalycotomine enantiomers. / Schönstein, László; Forró, E.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 24, No. 18, 30.09.2013, p. 1059-1062.

Research output: Contribution to journalArticle

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