Preparation of novel phenylfuran-based cyanohydrin esters

Lipase-catalysed kinetic and dynamic resolution

Csaba Paizs, Petri Tähtinen, Katri Lundell, L. Poppe, Florin Dan Irimie, Liisa T. Kanerva

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ≫100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.

Original languageEnglish
Pages (from-to)1895-1904
Number of pages10
JournalTetrahedron Asymmetry
Volume14
Issue number13
DOIs
Publication statusPublished - Jul 4 2003

Fingerprint

Enzyme kinetics
Lipases
Lipase
toluene
esters
Esters
Toluene
acylation
preparation
Kinetics
pseudomonas
kinetics
Antarctic regions
resins
acetone
Burkholderia cepacia
Acylation
Candida
decomposition
Acetone

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Preparation of novel phenylfuran-based cyanohydrin esters : Lipase-catalysed kinetic and dynamic resolution. / Paizs, Csaba; Tähtinen, Petri; Lundell, Katri; Poppe, L.; Irimie, Florin Dan; Kanerva, Liisa T.

In: Tetrahedron Asymmetry, Vol. 14, No. 13, 04.07.2003, p. 1895-1904.

Research output: Contribution to journalArticle

Paizs, Csaba ; Tähtinen, Petri ; Lundell, Katri ; Poppe, L. ; Irimie, Florin Dan ; Kanerva, Liisa T. / Preparation of novel phenylfuran-based cyanohydrin esters : Lipase-catalysed kinetic and dynamic resolution. In: Tetrahedron Asymmetry. 2003 ; Vol. 14, No. 13. pp. 1895-1904.
@article{c896b4410fd44f3ca3694f61ed29e1a8,
title = "Preparation of novel phenylfuran-based cyanohydrin esters: Lipase-catalysed kinetic and dynamic resolution",
abstract = "A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ≫100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.",
author = "Csaba Paizs and Petri T{\"a}htinen and Katri Lundell and L. Poppe and Irimie, {Florin Dan} and Kanerva, {Liisa T.}",
year = "2003",
month = "7",
day = "4",
doi = "10.1016/S0957-4166(03)00286-6",
language = "English",
volume = "14",
pages = "1895--1904",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "13",

}

TY - JOUR

T1 - Preparation of novel phenylfuran-based cyanohydrin esters

T2 - Lipase-catalysed kinetic and dynamic resolution

AU - Paizs, Csaba

AU - Tähtinen, Petri

AU - Lundell, Katri

AU - Poppe, L.

AU - Irimie, Florin Dan

AU - Kanerva, Liisa T.

PY - 2003/7/4

Y1 - 2003/7/4

N2 - A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ≫100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.

AB - A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ≫100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.

UR - http://www.scopus.com/inward/record.url?scp=0037805631&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037805631&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(03)00286-6

DO - 10.1016/S0957-4166(03)00286-6

M3 - Article

VL - 14

SP - 1895

EP - 1904

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 13

ER -