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

Bew, S.P., Ashford, P.-A. and Bachera, D.U. (2013) Synthesis of structure and function diverse α-D-diazoacetates, α-D-diazoacetamides, α-D-diazoketones, and the antibiotic α-D-azaserine. Synthesis, 45 (7). pp. 903-912. ISSN 0039-7881

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Abstract

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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: Pure Connector
Date Deposited: 02 Feb 2015 13:58
Last Modified: 21 Apr 2020 23:48
URI: https://ueaeprints.uea.ac.uk/id/eprint/51966
DOI: 10.1055/s-0032-1318136

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