Asymmetric synthesis has been a permanent interest of the group and has underpinned all aspects of our research, from the synthesis of unnatural amino acids through to the synthesis of alkaloids, nucleosides and terpenes. In particular we have developed a range of asymmetric organocatalytic processes. Organocatalysis is the term given to the field whereby transition metal ions are not used in the catalytic cycle. There are many benefits to this, including environmental and operational reasons. However, this approach is well suited to reactions using the nitro group in particular, which is a common feature for many of the reactions we have discovered. A major feature of the reaction processes we seek to develop is the generation of a high degree of molecular complexity from very simple starting materials. This is often achieved through "domino reactivity" - the name given to process where the formation of a first intermediate leads to the creation of one or more in a highly defined and controlled way, ultimately resulting in a complex and densely functionalised product.
1) Bryant, L. A.; Shankland, K.; Straker, H. E.; Johnston, C. D.; Lees, N. R.; Cobb, A. J. A. Enantioselective Organocatalytic Synthesis of Bicyclic Resorcinols via an Intramolecular Friedel−Crafts-Type 1,4-Addition: Access to Cannabidiol Analogues. Adv. Synth. Catal. 2021, 363, 4067.
2) Townsend, D.; Shankland, K.; Weymouth-Wilson, A.; Komsta, Z.; Evans, T.; Cobb, A. J. A. Highly Enantioselective, Organocatalytic, and Scalable Synthesis of a Rare cis,cis‐Tricyclic Diterpenoid. Chem. Eur. J., 2020, 26, 3504.
3) Al-Ani, W.; Shankland, K.; Cobb, A. J. A. Asymmetric Organocatalytic Synthesis of Cyclopentane γ-Nitroketones. Synlett, 2016, 27, 17.
4) Aitken, L. S.; Hammond, L. E.; Rajkumar, S.; Shankland, K.; Brown, G. D.; Cobb, A. J. A. Asymmetric cyclopropanation of conjugated cyanosulfones using a novel cupreine organocatalyst: rapid access to δ3-amino acids. Chem. Commun., 2015, 13558.
5) Rajkumar, S.; Shankland, K.; Brown, G. D.; Cobb, A. J. A. Organocatalytic enantioselective construction of nitrocyclohexanes containing multiple chiral centres via a cascade reaction. Chem. Sci., 2012, 3, 584.