- ISSN 0010-0765 printed
- ISSN 1212-6950 electronic
Prof. Pavel Kočovský, FRSE
60th Birthday - Foreword
A passion for chemistry! Nothing else can better characterise Pavel’s fruitful career in chemistry that he has successively accomplished in the former Czechoslovakia, Sweden and the United Kingdom. Although he has been a permanent resident in the UK since 1991, his ties with the Czech Republic have been strong and maintained all the time. Regardless of his location either in Prague, Uppsala, Leicester or Glasgow, he has always performed cutting-edge research in organic and organometallic chemistry always at the frontline of the competitive battlefields. Thus, as time went by, he has become an internationally recognised leader in reactivity control by neighbouring groups, he has contributed significantly to the establishment of the mechanistic bases and stereochemistry of transition metal catalysed reactions and he has quite rightfully been one of the leading experts in organocatalysis.
Let’s start from the very beginning. When Pavel was born in Rychnov nad Kněžnou, Czechoslovakia in 1951, Fairy Godmothers around the cradle predestined him to chemistry. Indeed, such a passion erupted already during his attendance at grammar school, when he built himself a functional laboratory in the basement of the parents’ cottage at Hradišťko, south of Prague, and carried out his first organic syntheses. Soon after he was enrolled at the Institute of Chemical Technology in Prague in 1969, he fell for chemistry entirely. He was enchanted by Professor Otakar Červinka, the guru of stereochemistry and asymmetric reactions in Prague at that time and the most visible personality at the department. Pavel attended his lectures for students of the fourth and fifth year not admitting he just entered the university. Professor Červinka recognised right away the bright talent and keen intellect of Pavel, who eventually carried out his Diploma Thesis under his supervision. As usual, such a coexistence of the two strong personalities produced sparks occasionally and some affairs became legendary.
Before Pavel graduated from the Institute of Chemical Technology in Prague (ICT) in 1974, he succeeded in starting his research activities also at the Institute of Organic Chemistry and Biochemistry of the Czechoslovak Academy of Sciences in Prague, which was located just a few hundred meters from the ICT. First, he collaborated with Dr. Želimír Procházka and then with Dr. Václav Černý, the head of the Department of Steroids, who supervised Pavel’s Ph.D. studies on the Westphalen rearrangement. At that time, Pavel was also influenced by Professor František Šorm, who was the founder of the Institute in the fifties and established a world-class research programme on natural products. After the defence of the Pavel’s Ph.D. Thesis at the Institute in 1977, a straightforward career of the young talented scientist to acquire experiences and inspirations abroad seemed to be logical but unfortunately this was not the case. After a bitter end of the Prague Spring in 1968, the political situation in the country was hopeless and the Czechoslovak Academy of Sciences was persecuted for its positive role in an attempt to humanise the communist regime. For Pavel as a young single man, who was not loyal to the regime, it was hard to travel or publish abroad. However, based on a personal intercession by his boss Dr. Václav Černý, Pavel finally received the permission to cross the Iron Curtain after a long six years to stay as a postdoctoral fellow with Professor John E. McMurry at Cornell University in 1983/1984. At that time, before leaving for the USA, Pavel was already internationally known for his significant contribution to the topic of neighbouring group participation in organic reactions. All these achievements were Pavel’s one-man show as he was barred from supervising students until the early eighties. However, during his stay at Ithaca Pavel acquainted himself with organometallics in organic synthesis and, immediately after his homecoming, he embarked on studying reactivity and the stereochemistry of metal catalysed reactions such as nucleophilic allylic substitution and cleavage of strained carbocycles. He was full of excitement about the newly emerged areas in modern organic chemistry and this resulted in lecturing by Pavel in organometallic chemistry and retrosynthetic analysis at the Institute of Organic Chemistry and Biochemistry (actually for the first time in the country) and also at Charles University in Prague. Another memory documents Pavel’s passion for chemistry, which he has considered a 24-hour job. Together with his friends of the same generation, all sharing a critical view of the political regime, Pavel co-organised private tea parties, which served as a natural platform to discuss broadly various aspects of chemistry. Then, along with two other members of this circle František Tureček (now Professor at University of Washington, Seattle) and Josef Hájíček (now at Zentiva/Sanofi, Prague), excellent chemists and Pavel’s friends, they wrote a book on stereoselective synthesis (Synthesis of Natural Products: Problems of Stereoselectivity, CRC 1986), which could be found on the shelves in many prominent laboratories worldwide.
In 1987, Pavel married Eva Šrámková, who graduated from Charles University in saccharide chemistry and collaborated with Pavel within a joint project on drug synthesis. This change in Pavel’s life contributed to his decision to accept an invitation by Professor Jan E. Bäckvall to stay in his laboratories at Uppsala, Sweden as Visiting Professor in 1989 since it helped, inter alia, to solve the burdensome problem with a flat in Prague. Actually, it was a lifetime decision to escape definitely and irreversibly together with the pregnant Eva from the communist camp in 1989 and to restart his career abroad. However, by the end of the same year, the Berlin Wall fell and the communist regime in Czechoslovakia collapsed too but Pavel’s successfully developing career in the Swedish environment, the possibilities to conduct independent research at Uppsala University and the everyday care of the newly born daughter, Elizabeth, (1990) kept Pavel in Uppsala during the sabbatical year.
In 1991, Pavel decided to move with his family to the UK as he accepted a position as Lecturer at the University of Leicester. His academic career in Leicester developed successfully: Pavel received the DSc degree (1993), was promoted to Reader (1993) and, finally, raised to the rank of full Professor (1999). During the Leicester period, Pavel continued in a fruitful and remarkably successful collaboration with Dr. Martin Smrčina at Charles University in Prague (now Sanofi-Aventis, Tucson, USA), the best Czech organic chemist of his generation. With other collaborators, Pavel contributed significantly, inter alia, to binaphthyl chemistry developing new approaches to original binaphthyl ligands, which they applied to catalysis emphasising mechanistic aspects. In addition, Pavel was also active in other areas including metal-complexes catalysed reactions (e.g., allylic substitution, cleavage of strained rings, Hartwig-Buchwald amination, carbonylation) and synthesis of natural products (e.g., estrone, tetrahydrocannabinol). However, most significantly, their second daughter, Veronica, was born in Leicester (1995).
In 1999, Pavel received an offer to accept the Sir William Ramsay Professor of Chemistry chair at the renowned University of Glasgow. Thus, Pavel’s family moved again, this time to Scotland. Although he continued in his study of transition metal catalysed reactions, he embarked mostly on newly emerged enantioselective organocatalysis as he immediately recognised its potential. Starting from scratch, Pavel rapidly reached the merit of being the leading expert in, e.g., asymmetric allylation of aldehydes with allyltrichlorosilanes catalysed by chiral pyridine N-oxides, organocatalytic reductive amination of α-chloro ketones or organocatalytic hydrosilylation of aromatic ketones and ketimines. He was remarkably successful with terpene-derived organocatalysts, which he provided intentionally with dignified acronyms when pronounced in English but having other meaning if pronounced in Czech (PINDY). Since the Leicester period, Pavel could closely collaborate with the excellent Russian chemist Andrei Malkov (now Professor at the Loughborough University, UK), who joined Pavel’s group in Glasgow.
During Pavel’s career, he supervised numerous students, postdoctoral associates and had many research fellows. Of those more than 90 co-workers, 22 hold or held academic positions and 5 of them received the Bader Award designated for young Czech organic chemists. In 2010, Pavel was elected to become a Fellow of the Royal Society of Edinburgh (FRSE), he is a Fellow of the Royal Society of Chemistry (FRSC, 1999), a member of the American Chemical Society (1981) and the Czech Chemical Society (1973). Pavel has served in Editorial Boards of Collect. Czech. Chem. Commun. (1999-2011), Curr. Org. Synth. (since 2003), J. Mol.Catal. (since 2007) and Appl. Organomet. Chem. (since 2008). Along with other professional memberships, Pavel was a member of the International Advisory Board of the Institute of Organic Chemistry and Biochemistry ASCR between 2003–2010 and consultant to Novo Nordisk (2002-2007). Furthermore, Pavel held several symposia chairs including the 15th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 15) that was hosted for the first time in the UK (Glasgow 2009).
Pavel is also a prolific author as he has so-far published over 200 original papers as well as review articles reaching over 5,000 citations (H-index 41), he has written or edited several monographs. He has delivered over 350 invited lectures at conferences, prominent universities or pharmaceutical/chemical companies worldwide. Three catalysts he developed have been commercialised.
All the time, Pavel has conducted highly innovative research being able to change the topic regularly and to reach a prominent position in the new field every time. Accordingly, his research interest covers a wide area of organic/organometallic synthesis and mechanisms, includes asymmetric catalysis, organocatalysis and the synthesis of biologically significant compounds and natural products. Pavel has strived not only to develop novel synthetic methods, in particular reactions mediated by transition/non-transition metals or organocatalysts but also to understand the background of the processes at the molecular level in collaboration with computational chemists. Perhaps most importantly, Pavel is an excellent and enthusiastic teacher initiating a deep interest in chemistry, who has significantly influenced already two younger generations of Czech organic chemists.
Many happy returns of the day, Pavel!
Ivo Starý
Institute of Organic Chemistry and Biochemistry AS CR
Prague
A selection of the 10 most prestigious papers of Professor Pavel Kočovský
1. Malkov A. V., Ramírez-López P., Biedermannová L., Rulíšek L., Dufková L., Kotora M., Zhu F., Kočovský P.: J. Am. Chem. Soc. 2008, 130, 5341-5348. On the Mechanism of Asymmetric Allylation of Aldehydes with Allyltrichlorosilanes Catalyzed by Quinox, a Chiral Isoquinoline N-Oxide.
2. Malkov A. V., Stončius S., Kočovský P.: Angew. Chem. Int. Ed. 2007, 46, 3722-3724. Enantioselective synthesis of 1,2-diarylaziridines via organocatalytic reductive amination of α-chloro ketones.
3. Malkov A. V., Stewart Liddon A. J. P., Ramirez-Lopez P., Bendová L., Haigh D., Kočovský P.: Angew. Chem. Int. Ed. 2006, 45, 1432-1435. Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines.
4. Malkov A. V., Dufková L., Farrugia L., Kočovský P.: Angew. Chem. Int. Ed. 2003, 42, 3674-3677. Quinox, a quinoline-type N-oxide, as organocatalyst in the asymmetric allylation of aromatic aldehydes with allyltrichlorosilanes: The role of arene-arene interactions.
5. Kočovský P., Vyskočil S., Císařová I., Sejbal J., Tišlerová I., Smrčina M., Lloyd-Jones G. C., Stephen S. C., Butts C. P., Murray M., Langer V.: J. Am. Chem. Soc. 1999, 121, 7714-7715. Palladium(II) complexes of 2-dimethylamino-2'-diphenylphosphino-1,1'-binaphthyl (MAP) with unique P,C(sigma)-coordination and their catalytic activity in allylic substitution, Hartwig-Buchwald amination, and Suzuki coupling.
6. Smrčina M., Vyskočil Š., Hanuš V., Polášek M., Langer V., Chew B. G. M., Zax D. B., Verrier H., Harper K., Claxton T. A., Kočovský P.: J. Am. Chem. Soc. 1996, 118, 487-488. The SN2 Reaction in the Solid State. An Unusual, Bal2 Aminolysis of an Ester Group in Crystalline (±)-2-Amino-2'-hydroxy-3'-(methoxycarbonyl)-1,1'-binaphthyl Elucidated by X-ray Diffraction and Isotopic Labeling. New Experimental Evidence for Linearity in SN2 Substitution.
7. Smrčina M., Poláková J., Vyskočil Š., Kočovský P.: J. Org. Chem. 1993, 58, 4534-4538. Synthesis of Enantiomerically Pure Binaphthyl Derivatives - Mechanism of the Enantioselective, Oxidative Coupling of Naphthols and Designing a Catalytic Cycle.
8. Kočovský P., Stieborová, I.: Tetrahedron Lett. 1989, 30, 4295-4298. Synthesis of Strophanthidin.
9. Starý I., Kočovský P.: J. Am. Chem. Soc. 1989, 111, 4981-4982. The First Observation of Syn-Anti Dichotomy in the Formation of (π-Allyl)palladium Complexes.
10. Kočovský P., Tureček F., Langer V., Podlahová J., Podlaha J.: J. Org. Chem. 1986, 51, 4888-4891. A Stereospecific Tandem Wagner-Meerwein Rearrangement in the Solvolysis of 19-Mesyloxy Steroids.
