Chemo and enantioselective addition of grignard reagents to ketones and enolizable
ketimines
Ortiz, Pablo
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Publication date: 2017
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Ortiz, P. (2017). Chemo and enantioselective addition of grignard reagents to ketones and enolizable ketimines. University of Groningen.
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Acknowledgements
231
moeizamer was in CH2Cl2 als in Et2O. Dit zou mogelijke gevolgen kunnen hebben
voor de katalyse.
Hoofdstuk 9 geeft een persoonlijk perspectief over het gebruik en de huidige
beperkingen van organometaal reagentia. Belangrijke recente ontwikkelingen worden besproken en enkele ideeën, geïnspireerd daarop, zijn getoetst in het lab.
Acknowledgements
This thesis is the result of a collective endeavor, and in these last pages I want to acknowledge and thank those who contributed to it.
Is not only custom but true feeling what dictates me to start thanking my supervisor, Prof. Syuzanna Harutyunyan. Dear Syuzi, thanks for being more an advisor than a boss. Your ideas and guidance have been key for the success of the projects. I am especially grateful for the imput that has helped me to become an independent researcher. I deeply appreciate the confidence you have put into me, as well as the freedom you have given me.
I would like to thank members of the reading committee, Prof. B. L. Feringa, Prof. H. Hiemstra and Prof. A. M. Minnaard, for your valuable remarks and approval of my thesis.
Some of the projects in this thesis were done in collaboration with other groups. A big thank you to Prof. M Erdelyi and his group in Gothenburg University -especially Patrik- for the collaboration detailed in chapter 8. Thanks for hosting me for two months and teaching me DOSY spectroscopy. It was an incredible experience both inside and outside the lab. Thanks too to Alavi, Inma, Linda, Daniel, Manuela, Carlo, Cassi, Tania, Alex and the rest at Kemivägen 4.
The VCD measurements described in chapter 4 were performed by the group of Prof. W. J. Buma at the University of Amsterdam. Thanks Paul, Mark and Angela for those experiments.
I have to acknowledge Prof. Otten for the X-ray crystallography data in chapter 7. Besides, thank you, Edwin, for the willingness to help me with quantum mechanical calculations.
I would also like to thank Pieter for the help with NMR, Hans for the help with the microwave synthesizer, Theodora for HRMS measurements and Monique for HPLC and CG-MS support. Tineke and Annette, your secretarial support is greatly appreciated.
The easy DFT calculations that I have learned to perform have been thanks to Davide and Steven. Thanks a lot! You are both excellent teachers with a lot of patience!
I am deeply grateful for the people that welcomed me at the Harutyunyan group. Francesca, thanks for introducing me around and helping me get started. Ana, your preliminary results with the diarylketones were the starting point of my first project, thanks for that. Alaric, thanks for the help in all the common projects. Antonio, it was most interesting having such a knowledgeable person around. With the arrival of new people colleagues became friends an Syuzi’s group evolved to the Sublime group. I am extremely happy to have shared time in and outside the lab with you guys. It was, as the name suggests, sublime.
Tilde and Juanfer, dear paranymphs: shortly stated you are good chemists and better persons. I am honoured to have your friendship and delighted that after these years together you will be walking with me one more time during the defence. Juafer, there is plenty I have to thank you. I feel that part of this thesis belongs to you too, being so many the projects that we have done together. Thanks for the discussions, the help with NMR, the corrections and an endless list of things you have helped me with. Tilde, your arrival at the group was a burst of enthusiasm, energy and joy. You are an extraordinary person and I am glad to have you as a friend. Francesco, we started at the same time and it has been a great experience to go through this journey together. Simone, having you around ensures a good mood and fun conversation. Rik, you were one of the first colleagues that became friend and I am glad that the friendship lasts. Thanks too for translating the summary. Johnny, your combination of hard-working and enjoying leisure time is unparallel and a model for me. Dima, supervising someone of your intelligence was a big challenge, sometimes I felt I was the student! Ravi, diligent in the lab and fun outside, it was a pleasure to work and chat with you. Mamen, it was relieving to share the worries of job search with someone in the same situation. Good that we both found something!
Giulia, you also qualify as a member of our group, as you spent more time in our office than in yours. I must say that I never enjoyed that much being disturbed than when you came to our office. To the rest of the current and old members of the group: Xingchen, Yafei, Eduarda, Daniel, Emilio, Natasha, Joost, Marieke, Renske, Filip, Kiril…it was a pleasure to meet you.
Organizing the Workweek in 2015 was a memorable experience, and I would like to thank Anouk and Giovanni for that.
One of the unique features of the Strating institute is the friendly atmosphere that goes beyond groups. It definitely contributes to coming happy to work, and is a great pool for new friends! It is impossible to go through the whole list of people that I have spent good time with during the PhD. If I ever shared a beer in the borrel or a chat in the corridor you are in my memory. Some of you are not only in my mind but also in my heart. Besides sharing workplace we had fun outside the institute, at dinners, trips and parties. You are now my friends and I hope to be so in the future: Ana, Ruben, Manuela, Annika, Lara, Liliana, Ivana, Cora, Sara, Sambika, Clemens, Nikola, Max, Matt, Ivana, Andreas, Gaël, Guille, Boris, Andrea-Nekane, Tao, Carlos, Valentín, Massimo, Ani, Matea, Jana, Michael, Francesco, Marco, Raquel, Francesca, Bea, Miriam, Mira, Varsha, Michele, Jonas. I do not forget the other friends outside the institute: Sergio, David, Héctor, Eduard, María Jesús, Gosia, Karina, Istvan.
If I ended up doing the PhD in Groningen it was only thanks to Dr. Javier Vicario. Javi, thanks first for guiding my transition from pharmacist to organic chemist. Second, thanks for suggesting me to come to Groningen and finally thanks for recommending me to Syuzi. It saved me from having to do a formal interview! I am also glad that you will be in my defence as a member of the examining committee. Dear Gerda, if I had not met you this thesis would probably have one more chapter, but I would definitely be less happy. Thanks for your understanding and support during the tough days at the lab. But I am even more thankful for the good moments that we have shared. Ik hou van jou.
I want to thank my whole family for their support during these years. Last lines are dedicated to those who raised me. Fredi Paiak, Bizkaiko Bertsolari Txapelketa irabazi zuenean aitari eskainitako agurrean holan esan zuen: "euskaraz eskaintzen dizut gure artean ez bezela/ itsas gizonen zeruan ziur ikasiko zenuela". Era berean, eskerrik asko aita txikitan nigan jakinmina pizteagatik. Ama, muchísimas gracias por inculcarme la necesidad de esforzarse, de mejorar y la confianza en mi mismo. Gracias por animarme a salir al extranjero y por apoyarme durante estos años. Te quiero.
Acknowledgements
233
The easy DFT calculations that I have learned to perform have been thanks to Davide and Steven. Thanks a lot! You are both excellent teachers with a lot of patience!
I am deeply grateful for the people that welcomed me at the Harutyunyan group. Francesca, thanks for introducing me around and helping me get started. Ana, your preliminary results with the diarylketones were the starting point of my first project, thanks for that. Alaric, thanks for the help in all the common projects. Antonio, it was most interesting having such a knowledgeable person around. With the arrival of new people colleagues became friends an Syuzi’s group evolved to the Sublime group. I am extremely happy to have shared time in and outside the lab with you guys. It was, as the name suggests, sublime.
Tilde and Juanfer, dear paranymphs: shortly stated you are good chemists and better persons. I am honoured to have your friendship and delighted that after these years together you will be walking with me one more time during the defence. Juafer, there is plenty I have to thank you. I feel that part of this thesis belongs to you too, being so many the projects that we have done together. Thanks for the discussions, the help with NMR, the corrections and an endless list of things you have helped me with. Tilde, your arrival at the group was a burst of enthusiasm, energy and joy. You are an extraordinary person and I am glad to have you as a friend. Francesco, we started at the same time and it has been a great experience to go through this journey together. Simone, having you around ensures a good mood and fun conversation. Rik, you were one of the first colleagues that became friend and I am glad that the friendship lasts. Thanks too for translating the summary. Johnny, your combination of hard-working and enjoying leisure time is unparallel and a model for me. Dima, supervising someone of your intelligence was a big challenge, sometimes I felt I was the student! Ravi, diligent in the lab and fun outside, it was a pleasure to work and chat with you. Mamen, it was relieving to share the worries of job search with someone in the same situation. Good that we both found something!
Giulia, you also qualify as a member of our group, as you spent more time in our office than in yours. I must say that I never enjoyed that much being disturbed than when you came to our office. To the rest of the current and old members of the group: Xingchen, Yafei, Eduarda, Daniel, Emilio, Natasha, Joost, Marieke, Renske, Filip, Kiril…it was a pleasure to meet you.
Organizing the Workweek in 2015 was a memorable experience, and I would like to thank Anouk and Giovanni for that.
One of the unique features of the Strating institute is the friendly atmosphere that goes beyond groups. It definitely contributes to coming happy to work, and is a great pool for new friends! It is impossible to go through the whole list of people that I have spent good time with during the PhD. If I ever shared a beer in the borrel or a chat in the corridor you are in my memory. Some of you are not only in my mind but also in my heart. Besides sharing workplace we had fun outside the institute, at dinners, trips and parties. You are now my friends and I hope to be so in the future: Ana, Ruben, Manuela, Annika, Lara, Liliana, Ivana, Cora, Sara, Sambika, Clemens, Nikola, Max, Matt, Ivana, Andreas, Gaël, Guille, Boris, Andrea-Nekane, Tao, Carlos, Valentín, Massimo, Ani, Matea, Jana, Michael, Francesco, Marco, Raquel, Francesca, Bea, Miriam, Mira, Varsha, Michele, Jonas. I do not forget the other friends outside the institute: Sergio, David, Héctor, Eduard, María Jesús, Gosia, Karina, Istvan.
If I ended up doing the PhD in Groningen it was only thanks to Dr. Javier Vicario. Javi, thanks first for guiding my transition from pharmacist to organic chemist. Second, thanks for suggesting me to come to Groningen and finally thanks for recommending me to Syuzi. It saved me from having to do a formal interview! I am also glad that you will be in my defence as a member of the examining committee. Dear Gerda, if I had not met you this thesis would probably have one more chapter, but I would definitely be less happy. Thanks for your understanding and support during the tough days at the lab. But I am even more thankful for the good moments that we have shared. Ik hou van jou.
I want to thank my whole family for their support during these years. Last lines are dedicated to those who raised me. Fredi Paiak, Bizkaiko Bertsolari Txapelketa irabazi zuenean aitari eskainitako agurrean holan esan zuen: "euskaraz eskaintzen dizut gure artean ez bezela/ itsas gizonen zeruan ziur ikasiko zenuela". Era berean, eskerrik asko aita txikitan nigan jakinmina pizteagatik. Ama, muchísimas gracias por inculcarme la necesidad de esforzarse, de mejorar y la confianza en mi mismo. Gracias por animarme a salir al extranjero y por apoyarme durante estos años. Te quiero.
