Synthetic methods: part (ii) oxidation and reduction methods

Abstract

This report highlights selected advances in some of the most commonly used oxidation and reduction reactions, focusing on the literature from 2012. The structure of this review follows that of the previous years report (J. K. Howard and C. J. T. Hyland, Annu. Rep. Prog. Chem., Sect. B: Org. Chem., 2012, 108, 29–52 (). In the field of oxidation a number of important advances have been made. Notably, the group of Miller has reported a peptide-based catalyst that allows the selective epoxidation of polyenes (P. A. Lichtor and S. J. Miller, Nat. Chem., 2012, 4, 990). Meanwhile, the Tomkinson group has reported osmium-free alkene dihydroxylation reactions with cyclopropyl-derived malonoyl peroxides (S. Picon, M. Rawling, M. Campbell and N. C. O. Tomkinson, Org. Lett., 2012, 14, 6250–6253). In the area of reduction methods the Chirik group has made an exciting breakthrough in the use of non-precious metal enantiopure C₁-symmetric bis(imino)pyridine cobalt complexes for asymmetric hydrogenation of a range of styrene derivatives in up to 96% ee (S. Monfette, Z. R. Turner, S. P. Semproni and P. J. Chirik, J. Am. Chem. Soc., 2012, 134, 4561–4564). Meanwhile Kuwano et al. have reported the first PhTrap-ruthenium catalysed asymmetric hydrogenation of naphthalenes (R. Kuwano, R. Morioka, M. Kashiwabara and N. Kameyama, Angew. Chem., Int. Ed., 2012, 51, 4136–4139).