Synthesis of structure and function diverse α-D-diazoacetates, α-D-diazoacetamides, α-D-diazoketones, and the antibiotic α-D-azaserine

S.P. Bew, P.-A. Ashford, D.U. Bachera

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Using 0.1 mol% to 1 mol% potassium carbonate in an acetonitrile-deuterium oxide mixture acts as a 'privileged' reaction system, which at ambient temperature affords, via a one-pot-one-cycle procedure, α-D-diazoacetates, α-D-diazoacetamides, or α-D-diazoketones from the corresponding nondeuterated form. The protocol is inexpensive, employs readily available materials, does not require harsh reaction conditions, requires two hours for completion, and affords the desired products in good yields and with excellent levels of deuterium incorporation. Exemplifying our protocol the first isotope labelled synthesis of N-Boc-α-D-azaserine with ≥95% D-incorporation is reported.
Original languageEnglish
Pages (from-to)903-912
Number of pages10
Issue number7
Publication statusPublished - 1 Jan 2013

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