Carbonyl 1,2-Transposition through Triflate-Mediated α-Amination

Guangbin Dong presents a method for carbonyl 1,2-transposition through α-amination.

Carbonyl groups – and their carbinol reduction products – are widespread in natural products, pharmaceutical agents, and other bio-related molecules. The location of the C–O functionality within a specific molecule is a key factor in determining its biological properties. For example, the C2-hydroxy analogue of ursolic acid displays 13-fold potency boost for inhibiting glycogen phosphorylase, relative to the parent compound. The group of Professor Guangbin Dong at the University of Chicago (USA) was interested in developing a synthetic method for selectively migrating a carbonyl oxygen within a given molecular structure, particularly to an adjacent carbon.

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