First PhD project at the University of Strasbourg

PhD Project Title: Asymmetric C(sp3)-H activation for the synthesis of chiral aliphatic building blocks for pharmaceutical and agrochemical applications

Principal Investigator: Dr. Joanna Wencel-Delord

http://syncat.unistra.fr

PhD Project description: Small, three-dimensional chiral molecules are attractive to pharmaceutical and agrochemical industries as increased selectivity and less side effects may be expected due to specific interactions of such compounds with enzymatic active sites. However, the synthesis of chiral, aliphatic alkane derivatives is far from trivial and reactions based on enantioselective C-H activation remain rare.[1] Yet, accessing alkanes motifs endowed of stereogenic centers via functionalization of simple, non-prefunctionalized substrates appears as one of the most straightforward and appealing strategies, as intermediately generated metallacycles can be potentially converted into a panel of congeners. Besides, such an approach offers new perspectives for late-stage functionalization of advanced intermediates.

Description of the work: ESR1 will develop, based on the expertise of the group and their recent results,[1] new chiral ligands promoting highly stereo-discriminant metalation of small alkane motifs of interest for the industrial partners. The attention will be focused on direct enantioselective functionalization of scaffolds bearing cycloalkane motifs. Once functionalization of simple substrates is achieved, the newly developed catalytic systems will be used, in collaboration with AstraZenec and Syngenta, for late stage functionalization drug- and agrochemical-like molecules.

Relevant skills that will be considered are:

  • Strong theoretical background and practical skills in organic synthesis and catalysis
  • Practical experience in analytical methods (NMR, MS, HPLC)
  • Good level of English proficiency (understood, spoken and written)
  • Skills in scientific writing (reports, papers, etc.)
  • Team spirit and collaborative predisposition

Planned secondments: “1 secondment (3 months) in AstraZeneca and 1 secondment in Syngenta

 

[1] Jerhaoui, S.; Djukic, J.-P.; Wencel-Delord, J.; Colobert, F. ACS Catal. 2019, 9, 2532–2542.

[1] For selected reviews see : a) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173–6214 ; b) Saint-Denis, T. G.; Zhu, R.-Y.; Chen, G.; Wu, Q.-F.; Yu, J.-Q. Science 2018, 359, 4798 ; c) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017, 117, 8908.

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