Functionalizing the ?-Position of ?-Diazo-?-ketoesters.

ABSTRACT: Although ?-diazo-?-ketoesters are synthetically versatile intermediates, methodology for introducing this functionality into complex molecules is still limited, most frequently involving a carboxylic acid precursor, which is then activated and transformed into a ?-ketoester, with the diazo group being subsequently added with a diazo transfer reagent. While introducing this highly functional moiety in a convergent one step process would be ideal, such an objective is limited by the relatively few studies which address functionalization of the ?-diazo-?-ketoester at the ?-position. In the present investigation, we evaluate strategies, both new and established, for functionalizing ?-diazo-?-ketoesters, particularly with regard to generating compounds prospectively useful in the synthesis of C1-substituted carbapenems. We report the first ?-aldehydo-?-diazo-?-ketoester as well as a method for its oxidation to the corresponding methyl ester, and the formation of a new substituted pyrazole under basic conditions.

SUBMITTER: Nguyen TQ 

PROVIDER: S-EPMC5147747 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature