Homogeneous Catalysis and Biomimetic Synthesis

Research line

Asymmetric synthesis is of crucial importance for modern drug discovery. The gap in the “chirality” (fraction of sp3 atoms) of synthesized compounds and accepted drugs is steadily increasing in the last decades, showing the urgent need for the development of novel approaches to chiral organic molecules.

The main goal of our group is to develop novel asymmetric synthetic tools, that will be efficient in terms of enantiomeric excess, regioselectivity and yield. Moreover, we aim to develop sustainable methods that allow researchers to build up molecular complexity in a short number of steps.

In order to address these challenges, our group has two research lines: Asymmetric Catalysis by Transition Metals Complexes and Biomimetic Synthesis of Natural Compounds.

Asymmetric Catalysis by Transition Metals Complexes

Asymmetric catalysis has a very attractive feature of utilizing only limited amounts of precious chiral materials (catalysts) in order to synthesize the bulk of chiral organic products, an approach that is both atom economical and sustainable. Although tremendous progress has been made in asymmetric catalysis in the last decades, the number of industrially applied chiral catalysts is rather limited.

Currently we focus on the development of a new family of chiral Ru(0) complexes for their further application in the fine chemical industry.

Biomimetic Synthesis of Natural Compounds

Natural compounds contain a large number of stereocenters. Realization of their total synthesis in an efficient manner provides natural products and their derivatives for medicinal studies. Total synthesis also benefits the general field of asymmetric synthesis through the development of novel methodologies for introducing, manipulating and multiplying chiral centers within a molecule.

The second research line focuses on the development of a unified biomimetic approach to different families of indole alkaloids.

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The group

Fedor Miloserdov (PI); Yifei Zhou; Natassa Lional (PhD student co-supervised with Han Zuilhof and Albada Bauke); TuNan Gao (co-supervised with Han Zuilhof, Guanna Li and Harry Bitter); Kelsey de Graaf (BSc student).

Former members

Clara Ansel (BSc student); Martijn Kerstens (BSc student); Stijn Kouwenberg (BSc student).

Teaching

·      ORC-30806 Structure and Reactivity (organic chemistry course for MSc students) – lecturing

·      BCT-35306 Catalysis and Sustainable Bio-Organic Synthesis (new MSc-level course starting in period 5, 2022) – coordination and lecturing

·      Advanced Organic Chemistry (VLAG course for PhD students) – coordination and lecturing

·      BSc/MSc Thesis Projects – several projects are currently available. Click here for details!

·      Organization of Internships – contact me if you’re interested in an organic synthesis internship in a chemical company or research institute. There are also possibilities to do internships at our group at ORC.

About Fedor

In August 2020 Fedor was appointed as assistant prof. at the Wageningen University (WUR) and became a member of the Laboratory of Organic Chemistry (ORC). Fedor has a background in synthetic organic and inorganic chemistry, and he applies his expertise in both areas in order to develop novel asymmetric transformations suitable for the fine chemical industry.

Fedor Miloserdov is originally from Russia and completed his undergraduate studies in Moscow. He then moved to Spain, where he did his PhD at the Institute of Chemical Research of Catalonia (ICIQ) with Prof. Vladimir Grushin in the areas of homogeneous catalysis, mechanistic studies and synthetic coordination chemistry. He completed his PhD Thesis in 2015, and remained at ICIQ for a postdoctoral stay with Prof. Antonio Echavarren working in the field of total synthesis of natural compounds. After that, he received a Marie Curie Fellowship and moved to the University of Bath (UK) in 2018-2020, where he worked with Prof. Mike Whittlesey in the area of synthetic organometallic chemistry.

Selected Publications (* denotes corresponding author)

1.      F. M. Miloserdov,* N. A. Rajabi, J. P. Lowe, M. F. Mahon, S. A. Macgregor* and M. K. Whittlesey*; Zn-Promoted C-H Reductive Elimination and H2 Activation via a Dual Unsaturated Heterobimetallic Ru-Zn Intermediate. J. Am. Chem. Soc. 2020, 142, 6340.

2.      F. M. Miloserdov,* C. J. Isaac, M. L. Beck, A. L. Burnage, J. C. B. Farmer, S. A. Macgregor,* M. F. Mahon and M. K. Whittlesey*; Impact of the Novel Z‑Acceptor Ligand Bis{(orthodiphenylphosphino)phenyl}zinc (ZnPhos) on the Formation and Reactivity of Low-Coordinate Ru(0) Centers. Inorg. Chem. 202059, 15606.

3.      N. O'Leary, F. M. Miloserdov,* M. Mahon* and M. K. Whittlesey*; Transforming PPh3 into Bidentate Phosphine Ligands at Ru-Zn Heterobimetallic Complexes. Dalton Trans. 2019, 48, 14000.

4.      F. M. Miloserdov, M. S. Kirillova, M. E. Muratore and A. M. Echavarren*; Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship. J. Am. Chem. Soc. 2018, 140, 5393.

5.      F. M. Miloserdov, D. McKay, B. K. Muñoz, H. Samouei, S. A. Macgregor* and V. V. Grushin*; Exceedingly Facile Ph–X Activation (X=Cl, Br, I) with Ruthenium(II): Arresting Kinetics, Autocatalysis, and Mechanisms. Angew. Chem. Int. Ed. 2015, 54, 8466.

6.      F. M. Miloserdov and V. V. Grushin*; Palladium-Catalyzed Aromatic Azidocarbonylation. Angew. Chem., Int. Ed. 2012, 51, 3668.