Exploring the application of diazocarbonyl compounds in ring opening reactions of epoxides for the synthesis of functionalized alcohols

Diazocarbonyl compounds have been extensively studied in cyclopropanation, cycloaddition, ylide formation, Wolff rearrangement and C-H or X-H insertion reactions, but its application as nucleophiles in substitution reactions is less explored so far.(1)
Epoxides present strong electrophilic nature and because of the three-membered strained ring they are susceptible to ring opening reactions by nucleophiles to produce bifunctional compounds of synthetic interest.(2) Our research group has been studying the development of method to provide functionalized alcohols by exploring the nucleophilicity of diazocarbonyl compounds in ring opening of epoxides.
In our initial screening, several Lewis acids and bases were evaluated with the goal to provide 2-diazo-4-hydroxy-carbonyl compounds. However, under the reaction conditions tested, instead of getting our desired compound we were only able to isolate the 2-diazo-3-hydroxy carbonyl compounds resulted from epoxide rearrangement. Further studies are in progress to suppress unwanted rearrangement rout and let the reaction lead us to our targeted compound.