natural products; organic synthesis; cycloaddition; antiviral compounds; cyclopropanes; alkaloids; cyclobutanes; stereoselective synthesis; enantioselective catalysis; cancer; antibiotics
Perrotta Daniele, Wang Ming-Ming, Waser Jérôme (2018), Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor-Acceptor meso -Diaminocyclopropanes, in Angewandte Chemie International Edition
, 57(18), 5120-5123.
Perrotta Daniele, Racine Sophie, Vuilleumier Jeremy, de Nanteuil Florian, Waser Jerome (2015), [4+2]-Annulations of Aminocyclobutanes, in ORGANIC LETTERS
, 17(4), 1030-1033.
Perrin Florian G., Kiefer Gregor, Jeanbourquin Loic, Racine Sophie, Perrotta Daniele, Waser Jerome, Scopelliti Rosario, Severin Kay (2015), 1-Alkynyltriazenes as Functional Analogues of Ynamides, in ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
, 54(45), 13393-13396.
de Nanteuil F., De Simone F., Frei R., Benfatti F., Serrano E., Waser J. (2014), Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes, in CHEMICAL COMMUNICATIONS
, 50(75), 10912-10928.
Serrano Eloisa, de Nanteuil Florian, Waser Jerome (2014), Diester-Substituted Aminocyclopropanes: Synthesis and Use in [3+2]-Annulation Reactions, in SYNLETT
, 25(16), 2285-2288.
de Nanteuil Florian, Serrano Eloisa, Perrotta Daniele, Waser Jerome (2014), Dynamic Kinetic Asymmetric [3+2] Annulation Reactions of Aminocyclopropanes, in JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
, 136(17), 6239-6242.
Racine Sophie, de Nanteuil Florian, Serrano Eloisa, Waser Jerome (2014), Synthesis of (Carbo) nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes, in ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
, 53(32), 8484-8487.
During the last century, synthetic organic chemistry has reached a high level of sophistication. The design of molecules can now been done on the molecular level, and synthetic organic compounds have become increasingly important for the study of biological systems, the cure of illnesses and the discovery of new organic materials. With the development of these applications and the understanding gained in them, the efficient synthesis of complex molecules has become even more important. Despite the great success of the last decades, organic chemistry is still a very time-consuming and expensive process. These difficulties limit applications to simple molecules that are easier to access, but probably not optimal for their intended task. In this context, it is absolutely essential to develop new synthetic tools to increase the flexibility and efficiency of organic synthesis.In particular, well-positioned nitrogen functionalities in rigid cyclic small molecules are expected to be ideally suited to interact with biological targets. This is clearly apparent in the impressive number of synthetic and natural bioactive compounds bearing nitrogen-rich cyclic scaffolds. Nevertheless, most commercial chemical libraries of synthetic compounds are limited to relatively flat heterocycles and lack tridimensional complexity, which is essential for selective interactions with enzymes and receptors. In this project we will make use of the strain energy of small rings and the high reactivity of enamides for the synthesis of carbocycles and heterocycles based on formal cycloaddition reactions. More specifically, we intend to use the desired nitrogen functionality itself to modulate the reactivity of the small ring or double bond and allow its activation under mild catalytic conditions. This will lead to the development of highly diastereoselective and enantioselective methods for the synthesis of nitrogen-substituted carbo- and heterocycles, with ring size ranging from four to seven atoms. The obtained building blocks will match perfectly with the complex core of important bioactive natural alkaloids and synthetic antibiotic and antiviral compounds. The high convergence and efficiency of the reaction will be ideally suited for the synthesis of focused library with high potential for the discovery of new bioactive compounds.