Functionalizing the γ-position of α-diazo-β-ketoesters

Thu Q. Nguyen, Maha Alqurafi, Cash Edwards, Pauline Nguyen, Jean Kim, Samuel Casco, Maricka Bennet, Christopher Chiang, Maureen Lohry, Melina Cox, Byron Meshram, Duyen Le, Eugene Kim, Snigdha Smriti, Peter Oelschlaeger, John D. Buynak

Research output: Contribution to journalArticlepeer-review

Abstract

Although α-diazo-β-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 β-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 α-diazo-β-ketoester at the γ-position. In the present investigation, we evaluate strategies, both new and established, for functionalizing α-diazo-β-ketoesters, particularly with regard to generating compounds prospectively useful in the synthesis of C1-substituted carbapenems. We report the first δ-aldehydo-α-diazo-β-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.

Original languageEnglish
Pages (from-to)3330-3333
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number30
DOIs
StatePublished - 2016
Externally publishedYes

Keywords

  • Carbapenem
  • Diazo
  • Pyrazole
  • β-Ketoester

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