The use of nitrile oxides bearing a masked β-oxo group as β-hydroxy-3-oxopropionylating agents for the vicinal functionalization of olefins is described. The β-hydroxy ketones revealed on hydrogenation of the initially formed 1,3-dipolar cycloaddition products undergo zinc triflate promoted cyclocondensation to 2,3-dihydropyran-4-ones, useful carbohydrate building blocks. The application of this chemistry to the preparation of a protected form of “compactin lactone” is detailed.
ASJC Scopus subject areas
- Organic Chemistry