Home / Publications / Aerobic asymmetric oxygenation catalysis: a well forgotten… future?

Aerobic asymmetric oxygenation catalysis: a well forgotten… future?

Konstantin Petrovich Bryliakov 1
Konstantin Petrovich Bryliakov
10.1016/j.mencom.2021.01.002
Published 2020-12-30
Focus article , Volume 31, Issue 1, 8-13
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Bryliakov K. P. Aerobic asymmetric oxygenation catalysis: a well forgotten… future? // Mendeleev Communications. 2020. Vol. 31. No. 1. pp. 8-13.
GOST all authors (up to 50) Copy
Bryliakov K. P. Aerobic asymmetric oxygenation catalysis: a well forgotten… future? // Mendeleev Communications. 2020. Vol. 31. No. 1. pp. 8-13.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.01.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.002
TI - Aerobic asymmetric oxygenation catalysis: a well forgotten… future?
T2 - Mendeleev Communications
AU - Bryliakov, Konstantin Petrovich
PY - 2020
DA - 2020/12/30
PB - Mendeleev Communications
SP - 8-13
IS - 1
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Bryliakov,
author = {Konstantin Petrovich Bryliakov},
title = {Aerobic asymmetric oxygenation catalysis: a well forgotten… future?},
journal = {Mendeleev Communications},
year = {2020},
volume = {31},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.002},
number = {1},
pages = {8--13},
doi = {10.1016/j.mencom.2021.01.002}
}
MLA
Cite this
MLA Copy
Bryliakov, Konstantin Petrovich. “Aerobic asymmetric oxygenation catalysis: a well forgotten… future?.” Mendeleev Communications, vol. 31, no. 1, Dec. 2020, pp. 8-13. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.01.002.
Views / Downloads
1 / 3

Keywords

asymmetric catalysis
dioxygen
Green chemistry
mechanism
transition metal complexes

Abstract

Aerobic dioxygen, the cheapest oxidant with the highest active oxygen content, has so far remained underrepresented in selective, including stereoselective, oxidation catalysis. This article surveys the milestones in the area of catalytic asymmetric oxidations of organic molecules leading to formation of new C–O or X–O bonds, reported in the last decades. The existing catalyst systems are outlined, and technical as well as fundamental difficulties that hamper widespread adoption of dioxygen into asymmetric oxygenation catalysis are discussed.

References

1.
10.1016/j.mencom.2021.01.002_bib0005
Gale
Astrobiology of Earth: the Emergence, Evolution and Future of Life on a Planet in Turmoil, 2009
2.
https://www.atmos.washington.edu/∼dennis/321/Chapter_01_Tables.pdf.
3.
10.1016/j.mencom.2021.01.002_bib0015
Strukul
Liquid Phase Oxidation via Heterogeneous Catalysis, 2013
4.
Alkane Oxidation: Methane Monooxygenases, Related Enzymes, and Their Biomimetics.
Wang V.C., Maji S., Chen P.P., Lee H.K., Yu S.S., Chan S.I.
Chemical Reviews, 2017
5.
Dioxygen in Polyoxometalate Mediated Reactions.
Weinstock I.A., Schreiber R.E., Neumann R.
Chemical Reviews, 2017
6.
Aerobic Oxidations of Light Alkanes over Solid Metal Oxide Catalysts.
Grant J.T., Venegas J.M., McDermott W.P., Hermans I.
Chemical Reviews, 2017
7.
Homogeneous Oxygenase Catalysis
Liang Y., Wei J., Qiu X., Jiao N.
Chemical Reviews, 2018
13.
Catalytic asymmetric oxidations using molecular oxygen
Ottenbacher R.V., Talsi E.P., Bryliakov K.P.
Russian Chemical Reviews, 2018
14.
10.1016/j.mencom.2021.01.002_bib0070
Groves
Cytochrome P450: Structure, Mechanism, and Biochemistry, 2005
15.
Structure and Chemistry of Cytochrome P450
Denisov I.G., Makris T.M., Sligar S.G., Schlichting I.
Chemical Reviews, 2005
22.
Aerobic Copper-Catalyzed Organic Reactions
Allen S.E., Walvoord R.R., Padilla-Salinas R., Kozlowski M.C.
Chemical Reviews, 2013
23.
Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions.
Wang D., Weinstein A.B., White P.B., Stahl S.S.
Chemical Reviews, 2017
26.
Enantioselective oxidation of aromatic ketones by molecular oxygen, catalyzed by chiral monoaza-crown ethers
de Vries E.F., Ploeg L., Colao M., Brussee J., van der Gen A.
Tetrahedron Asymmetry, 1995
27.
The Direct Amino Acid-Catalyzed Asymmetric Incorporation of Molecular Oxygen to Organic Compounds
Córdova A., Sundén H., Engqvist M., Ibrahem I., Casas J.
Journal of the American Chemical Society, 2004
28.
Direct Amino Acid Catalyzed Asymmetric α Oxidation of Ketones with Molecular Oxygen
Sundén H., Engqvist M., Casas J., Ibrahem I., Córdova A.
Angewandte Chemie - International Edition, 2004
32.
Pentanidium-catalyzed enantioselective α-hydroxylation of oxindoles using molecular oxygen.
Yang Y., Moinodeen F., Chin W., Ma T., Jiang Z., Tan C.
Organic Letters, 2012
36.
Bifunctional Photocatalysts for Enantioselective Aerobic Oxidation of β-Ketoesters
Ding W., Lu L., Zhou Q., Wei Y., Chen J., Xiao W.
Journal of the American Chemical Society, 2016
37.
Bifunctional metal-free photo-organocatalysts for enantioselective aerobic oxidation of β-dicarbonyl compounds
Tang X., Feng S., Wang Y., Yang F., Zheng Z., Zhao J., Wu Y., Yin H., Liu G., Meng Q.
Tetrahedron, 2018
39.
Visible Light‐Induced Salan‐Copper(II)‐Catalyzed Enantioselective Aerobic α‐Hydroxylation of β‐Keto Esters
Yang F., Zhao J., Tang X., Wu Y., Yu Z., Meng Q.
Advanced Synthesis and Catalysis, 2019
42.
Aerobic Enantioselective Epoxidation of Unfunctionalized Olefins Catalyzed by Optically Active Salen–Manganese (III) Complexes
Yamada T., Imagawa K., Nagata T., Mukaiyama T.
Bulletin of the Chemical Society of Japan, 1994
47.
Recent Advances in Aerobic Oxygenation
Mukaiyama T., Yamada T.
Bulletin of the Chemical Society of Japan, 1995
48.
Enantioselective Aerobic Oxidation of Sulfides Catalyzed by Optically Activeβ-Oxo Aldiminatomanganese(III) Complexes
Nagata T., Imagawa K., Yamada T., Mukaiyama T.
Bulletin of the Chemical Society of Japan, 1995
50.
Photopromoted Ru-Catalyzed Asymmetric Aerobic Sulfide Oxidation and Epoxidation Using Water as a Proton Transfer Mediator
Tanaka H., Nishikawa H., Uchida T., Katsuki T.
Journal of the American Chemical Society, 2010
51.
Asymmetric Epoxidation of Conjugated Olefins with Dioxygen
Koya S., Nishioka Y., Mizoguchi H., Uchida T., Katsuki T.
Angewandte Chemie - International Edition, 2012
55.
Metal-catalysed enantiospecific aerobic oxidation of cyclobutanones
Bolm C., Schlingloff G.
Journal of the Chemical Society Chemical Communications, 1995
57.
The First 200-L Scale Asymmetric Baeyer−Villiger Oxidation Using a Whole-Cell Biocatalyst
Baldwin C.V., Wohlgemuth R., Woodley J.M.
Organic Process Research and Development, 2008
58.
Applications of Baeyer-Villiger Monooxygenases in Organic Synthesis
Alphand V., Wohlgemuth R.
Current Organic Chemistry, 2010
59.
Asymmetric dihydroxylation via ligand-accelerated catalysis
Jacobsen E.N., Marko I., Mungall W.S., Schroeder G., Sharpless K.B.
Journal of the American Chemical Society, 1988
61.
Dihydroxylation of olefins using air as the terminal oxidant
Döbler C., Mehltretter G.M., Sundermeier U., Beller M.
Journal of Organometallic Chemistry, 2001
62.
https://www.nobelprize.org/prizes/chemistry/2001/press-release/.
63.
10.1016/j.mencom.2021.01.002_bib0315
Bryliakov
Environmentally Sustainable Catalytic Asymmetric Oxidations, 2015
64.
Holy Grails of Chemistry
Bard A.J., Whitesides G.M., Zare R.N., McLafferty F.W.
Accounts of Chemical Research, 1995
65.
10.1016/j.mencom.2021.01.002_bib0325
Bryliakov
Frontiers of Green Catalytic Selective Oxidations, 2019