References

Su, S.; Seiple, I.B.; Young, I. S.; Baran, P.S. J. Am. Chem. Soc. 2008, 130, 16490–16491.

This paper shows the transformation of molecules that are very similar to molecules 8 to 10, via chemeoselective silver(II) oxidation. They explain the biological benefits of the molecule that is formed, which include: immunosuppressant, cytotoxic, anti-fungal and anti-inflammatory. Molecules such as 10 are extremely useful because they are very polar, they have a compact arrangement of functional groups and they are very complex on a stereochemical level. All of these aspects make them very attractive to chemists, specifically for biological purposes. The paper then goes on to explain the method of removing the Boc groups, as seen in steps 7 to 8, was due to addition of aqueous trifluoroacetic acid. Once the nitrogens have been deprotected, they are able to react with the silver(II) picolinate and 10% aqueous TFA. This causes an oxidation to take place at an sp3 carbon, which essentially causes a hydrogen to be replaced by an OH group. Finally, the paper describes the experimental procedure for the reaction.

Baran, P. S.; Newhouse, T. Angew. Chem. Int. Ed. Engl. 2004, 50, 3362-3374.

This paper discusses the selectivity of carbon-hydrogen bond oxidation. This is very helpful in analyzing the selection of the particular C-H bond that was oxidized by silver(II) picolinate in our reaction.

Shenvi, R. A.; O’Malley, D. P.; Baran, P. S. Acc. Chem. Res. 2009, 42, 530-541.

This paper discusses the importance of silver(II) picolinate as an oxidation agent of carbon-hydrogen bonds. It takes a look at our specific reaction of 7 to 10 and explains that it is so ideal, because it gives a 40% yield with a 3:1 mixture of the diastereomers, which could then be separated. This is important in knowing how to reproduce our experiment.

Xia, J. B.; Cormier, K. W.; Chen, C. Chem. Sci. 2012, 3, 2240-2245.

This paper discusses the importance of transition metal catalysts for carbon-hydrogen bond oxidation. It explains that the use of transition metals as catalysts allows for an oxidation that is more selective an efficient.