Research funded by ERC-consolidator grant “BENOVELTY” (101000893)
In this project, we plan to develop novel saturated bioisosteres of benzenes:
Publications on the ERC-project
14) Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations
V. Ripenko, V. Sham, V. Levchenko, S. Holovchuk, D. Vysochyn, I. Klymov, D. Kyslyi, S. Veselovych, S. Zhersh, Y. Dmytriv, A. Tolmachev, I. Sadkova, I. Pishel, K. Horbatok, V. Kosach, Y. Nikandrova, P. K. Mykhailiuk*
Nat. Synth. 2024, 3, 1538–1549
![Light-enabled scalable synthesis of bicyclo[1.1.1]pentane halides and their functionalizations](https://mykhailiukchem.org/wp-content/uploads/2024/11/171.png)
13) 2-Oxabicyclo[2.1.1]hexanes: synthesis, properties and validation as bioisosteres of ortho- and meta-Benzenes
V. V. Levterov, Y. Panasiuk, O. Shablykin, O. Stashkevych, K. Sahun, A. Rassokhin, I. Sadkova, D. Lesyk, A. Anisiforova, Y. Holota, P. Borysko, I. Bodenchuk, N. M. Voloshchuk, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2024, 63, e202319831
![2-Oxabicyclo[2.1.1]hexanes: synthesis, properties and validation as bioisosteres of ortho- and meta-Benzenes](https://mykhailiukchem.org/wp-content/uploads/2024/02/164.png)
12) Spiro[3.3]heptane as a Saturated Benzene Bioisostere
K. Prysiazhniuk, O. P. Datsenko, O. Polishchuk, S. Shulha, O. Shablykin, Y. Nikandrova, K. Horbatok, I. Bodenchuk, P. Borysko, D. Shepilov, I. Pishel, V. Kubyshkin, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2024, 63, e202316557
![Spiro[3.3]heptane as a Saturated Benzene Bioisostere](https://mykhailiukchem.org/wp-content/uploads/2024/02/162.png)
11) Borylated cyclobutanes via thermal [2 + 2]-cycloaddition
K. Prysiazhniuk, O. Polishchuk, S. Shulha, K. Gudzikevych, O. P. Datsenko, V. Kubyshkin, P. K. Mykhailiuk*
Chem. Sci. 2024, 15, 3249-3254
![Borylated cyclobutanes via thermal [2 + 2]-cycloaddition](https://mykhailiukchem.org/wp-content/uploads/2024/02/160.png)
10) 1-Azaspiro[3.3]heptane as a Bioisostere of Piperidine
A. A. Kirichok, H. Tkachuk, Y. Kozyriev, O. Shablykin, O. Datsenko, D. Granat, T. Yegorova, Y. P. Bas, V. Semirenko, I. Pishel, V. Kubyshkin, D. Lesyk, O. Klymenko-Ulianov, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2023, 62, e202311583
![1-Azaspiro[3.3]heptane as a Bioisostere of Piperidine](https://mykhailiukchem.org/wp-content/uploads/2024/02/158.png)
9) 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene
V. A. Denisenko, P. Garbuz, Y. Makovetska, O. Shablykin, D. Lesyk, G. Al-Maali, R. Korzh, I. V. Sadkova, P. K. Mykhailiuk*
Chem. Sci. 2023, 14, 14092-14099
![1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of ortho-substituted benzene](https://mykhailiukchem.org/wp-content/uploads/2024/02/157.png)
8) 2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring
V. V. Levterov, Y. Panasiuk, K. Sahun, O. Stashkevych, V. Badlo, O. Shablykin, I. Sadkova, L. Bortnichuk, O. Klymenko-Ulianov, Y. Holota, L. Lachmann, P. Borysko, K. Horbatok, I. Bodenchuk, Y. Bas, D. Dudenko, P. K. Mykhailiuk*
Nat. Commun. 2023, 14, 5608
![2-Oxabicyclo[2.2.2]octane as a new bioisostere of the phenyl ring](https://mykhailiukchem.org/wp-content/uploads/2023/10/156.png)
7) 2-Oxabicyclo[2.1.1]hexanes as saturated bioisosteres of the ortho-substituted phenyl ring
A. Denisenko, P. Garbuz, N. M. Voloshchuk, Y. Holota, P. K. Mykhailiuk*
Nat. Chem. 2023, 15, 1155–1163
6) General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Bioisosteres
D. Dibchak, M. Snisarenko, A. Mishuk, O. Shablykin, L. Bortnichuk, O. Klymenko-Ulianov, Y. Kheylik, I. V. Sadkova, H. S. Rzepa, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2023, 62, e202304246
![General Synthesis of 3-Azabicyclo[3.1.1]heptanes and Evaluation of Their Properties as Saturated Bioisosteres](https://mykhailiukchem.org/wp-content/uploads/2023/06/154.png)
5) Rapid and scalable halosulfonylation of strain-release reagents
H. D. Pickford, V. Ripenko, R. E. McNamee, S. Holovchuk, A. L. Thompson, R. C. Smith, P. K. Mykhailiuk,* E. A. Anderson*
Angew. Chem. Int. Ed. 2023, 62, e202213508
4) A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes
R. Bychek, P. K. Mykhailiuk*
Angew. Chem. Int. Ed. 2022, 61, e202205103
![A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes](https://mykhailiukchem.org/wp-content/uploads/2022/10/147.png)
3) Unexpected Isomerization of Oxetane-Carboxylic Acids
B. Chalyk, A. Grynyova, K. Filimonova, T. V. Rudenko, D. Dibchak, P. K. Mykhailiuk*
Org. Lett. 2022, 24, 4722-4728
2) Oxa-spirocycles: synthesis, properties and applications
K. Fominova, T. Diachuk, D. Granat, T. Savchuk, V. Vilchynskyi, O. Svitlychnyi, V. Meliantsev, I. Kovalchuk, E. Litskan, V. V. Levterov, V. R. Badlo, R. I. Vaskevych, A. I. Vaskevych, A. V. Bolbut, V. V. Semeno, R. Iminov, K. Shvydenko, A. S. Kuznetsova, Y. V. Dmytriv, D. Vysochyn, V. Ripenko, A. A. Tolmachev, O. Pavlova, H. Kuznietsova, I. Pishel, P. Borysko, P. K. Mykhailiuk*
Chem. Sci. 2021, 12, 11294-11305
1) Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)
V. Ripenko, D. Vysochyn, I. Klymov, S. Zhersh, P. K. Mykhailiuk*
J. Org. Chem. 2021, 86, 14061-14068
![Large-Scale Synthesis and Modifications of Bicyclo[1.1.1]pentane-1,3-dicarboxylic Acid (BCP)](https://mykhailiukchem.org/wp-content/uploads/2021/11/140.png)
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