Our latest paper appeared online yesterday in the Journal of the American Chemical Society. The article describes the results of a detailed study of sulfur ylide epoxidations and aziridinations using a cheap and readily available chiral sulfide (isothiocineole). The sulfide can be made in one step from sulfur and limonene, and is commercially available as either enantiomer (e.g., Aldrich cat 766429; TCI T2578 and T2579). Enantiopure epoxides and aziridines can be easily made using this method which has already been applied in the synthesis of biologically active molecules following our 2010 communication (e.g., OL2011, ACIE 2011) This work is part of a long-standing collaboration with Prof Varinder Aggarwal at University of Bristol, and is a real team effort – well done everybody!
The paper can be read online here:
J Am Chem Soc, 2013, asap article. DOI: 10.1021/ja405073w
Open Access: If you do not have a J Am Chem Soc subscription please email Eoghan for a free access code for this article via ACS Articles on Request.
We thank EPSRC, the University of Bristol, Departament d’Educacio I Universitats de la Generalitat de Catalunya, Science Foundation Ireland and Marie-Curie COFUND for support.
J Am Chem Soc is the most cited journal in chemistry and the flagship journal of the American Chemical Society.
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