Rapid Access to α-Alkoxy and α-Amino Acid Derivatives through Safe Continuous-Flow Generation of Diazoesters

    • Hannah E. Bartrum1
    • David C. Blakemore2
    • Christopher J. Moody1
    • Christopher J. Hayes1
    • 1School of Chemistry, University of Nottingham, UK
    • 2Pfizer Global Research and Development, Sandwich, UK

    Microreactors: A highly efficient continuous-flow process has been developed for the synthesis of diazoesters from arylsulfonylhydrazones by means of in-flow Bamford–Stevens reactions. Furthermore, a range of α-alkoxy and α-amino acid derivatives have been prepared in excellent yields through rhodium(II)-mediated O[BOND]H and N[BOND]H insertions, without the need to isolate or handle the potentially hazardous diazo species (see scheme).

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