A new strategy for the catalytic enantioselective α-arylation of N-acyloxazolidinones with chiral copper(II)-bisoxazoline complexes and diaryliodonium salts is described. The mild catalytic conditions are operationally simple, produce valuable synthetic building blocks in excellent yields and enantioselectivities, and can be applied to the synthesis of important nonsteroidal anti-inflammatory agents and their analogues.

The development of new antimalarial compounds remains a pivotal part of the strategy for malaria elimination. Recent large-scale phenotypic screens have provided a wealth of potential starting points for hit-to-lead campaigns. One such public set is explored, employing an open source research mechanism in which all data and ideas were shared in real time, anyone was able to participate, and patents were not sought. One chemical subseries was found to exhibit oral activity but contained a labile ester that could not be replaced without loss of activity, and the original hit exhibited remarkable sensitivity to minor structural change. A second subseries displayed high potency, including activity within gametocyte and liver stage assays, but at the cost of low solubility. As an open source research project, unexplored avenues are clearly identified and may be explored further by the community; new findings may be cumulatively added to the present work.

SUMMARYOpen science is a new concept for the practice of experimental laboratory-based research, such as drug discovery. The authors have recently gained experience in how to run such projects and here describe some straightforward steps others may wish to take towards more openness in their own research programmes. Existing and inexpensive online tools can solve many challenges, while some psychological barriers to the free sharing of all data and ideas are more substantial.

Chemical scientists’ experiences with LabTrove.

Enantioselective α-Arylation of N-Acyloxazolidinones with Copper(II)-Bisoxazoline Catalysts and Diaryliodonium Salts. -A variety of N-acyloxazolidinones is applied to the reaction with the mesityl(phenyl)iodonium triflate to afford the α-phenylated products with high yields and enantioselectivities. Arylsubstituted silylketenimide (IV) affords the product (V) with the opposite configuration compared to (III). A wide range of diaryliodonium salts (VI) are tested showing sensitivity to the steric effects which reduce the enantioselectivity [cf. (VII)]. -(BIGOT, A.; WILLIAMSON, A. E.; GAUNT*, M. J.; J. Am. Chem. Soc. 133 (2011) 35, 13778-13781, http://dx.