Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches

Annemarie Hage, Daniëlle G I Petra, James A Field, Dick Schipper, Joannes B P A Wijnberg, Paul C J Kamer, Joost N H Reek, Piet W N M Van Leeuwen, Ron Wever, Hans E. Schoemaker

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)-amino alcohol and iridium(I)-amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98%). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol.

Original languageEnglish (US)
Pages (from-to)1025-1034
Number of pages10
JournalTetrahedron Asymmetry
Volume12
Issue number7
DOIs
StatePublished - May 8 2001

Fingerprint

bioconversion
Bioconversion
Hydrogenation
Ketones
ketones
hydrogenation
alcohols
Alcohols
cells
Unsaturated compounds
Amino alcohols
Amino Alcohols
Iridium
Ruthenium
fungi
Enantioselectivity
Coordination Complexes
Sulfides
iridium
Fungi

ASJC Scopus subject areas

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

Cite this

Hage, A., Petra, D. G. I., Field, J. A., Schipper, D., Wijnberg, J. B. P. A., Kamer, P. C. J., ... Schoemaker, H. E. (2001). Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches. Tetrahedron Asymmetry, 12(7), 1025-1034. https://doi.org/10.1016/S0957-4166(01)00172-0

Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation : Complementary approaches. / Hage, Annemarie; Petra, Daniëlle G I; Field, James A; Schipper, Dick; Wijnberg, Joannes B P A; Kamer, Paul C J; Reek, Joost N H; Van Leeuwen, Piet W N M; Wever, Ron; Schoemaker, Hans E.

In: Tetrahedron Asymmetry, Vol. 12, No. 7, 08.05.2001, p. 1025-1034.

Research output: Contribution to journalArticle

Hage, A, Petra, DGI, Field, JA, Schipper, D, Wijnberg, JBPA, Kamer, PCJ, Reek, JNH, Van Leeuwen, PWNM, Wever, R & Schoemaker, HE 2001, 'Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches', Tetrahedron Asymmetry, vol. 12, no. 7, pp. 1025-1034. https://doi.org/10.1016/S0957-4166(01)00172-0
Hage, Annemarie ; Petra, Daniëlle G I ; Field, James A ; Schipper, Dick ; Wijnberg, Joannes B P A ; Kamer, Paul C J ; Reek, Joost N H ; Van Leeuwen, Piet W N M ; Wever, Ron ; Schoemaker, Hans E. / Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation : Complementary approaches. In: Tetrahedron Asymmetry. 2001 ; Vol. 12, No. 7. pp. 1025-1034.
@article{4dc5807d413f4db1bfe24b2538508748,
title = "Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches",
abstract = "Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)-amino alcohol and iridium(I)-amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98{\%}). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol.",
author = "Annemarie Hage and Petra, {Dani{\"e}lle G I} and Field, {James A} and Dick Schipper and Wijnberg, {Joannes B P A} and Kamer, {Paul C J} and Reek, {Joost N H} and {Van Leeuwen}, {Piet W N M} and Ron Wever and Schoemaker, {Hans E.}",
year = "2001",
month = "5",
day = "8",
doi = "10.1016/S0957-4166(01)00172-0",
language = "English (US)",
volume = "12",
pages = "1025--1034",
journal = "Tetrahedron Asymmetry",
issn = "0957-4166",
publisher = "Elsevier Limited",
number = "7",

}

TY - JOUR

T1 - Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation

T2 - Complementary approaches

AU - Hage, Annemarie

AU - Petra, Daniëlle G I

AU - Field, James A

AU - Schipper, Dick

AU - Wijnberg, Joannes B P A

AU - Kamer, Paul C J

AU - Reek, Joost N H

AU - Van Leeuwen, Piet W N M

AU - Wever, Ron

AU - Schoemaker, Hans E.

PY - 2001/5/8

Y1 - 2001/5/8

N2 - Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)-amino alcohol and iridium(I)-amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98%). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol.

AB - Prochiral aryl and dialkyl ketones were enantioselectively reduced to the corresponding alcohols using whole cells of the white-rot fungus Merulius tremellosus ono991 as a biocatalytic reduction system and ruthenium(II)-amino alcohol and iridium(I)-amino sulfide complexes as metal catalysts in asymmetric transfer hydrogenation. Comparison of the results showed that the corresponding chiral alcohols could be obtained with moderate to high enantioselectivities (e.e.s of up to 98%). The biocatalytic and transfer hydrogenation approaches appear to be complementary. The biocatalytic approach is the most suitable for the enantioselective reduction of chloro-substituted (aryl) ketones, whereas in the reduction of α,β-unsaturated compounds excellent results were obtained using the catalytic hydrogenation protocol.

UR - http://www.scopus.com/inward/record.url?scp=0035826605&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035826605&partnerID=8YFLogxK

U2 - 10.1016/S0957-4166(01)00172-0

DO - 10.1016/S0957-4166(01)00172-0

M3 - Article

AN - SCOPUS:0035826605

VL - 12

SP - 1025

EP - 1034

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

SN - 0957-4166

IS - 7

ER -