1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)₄]PF₆: A Novel Approach to β-Amino (E)-Enylphosphonates

Abstract

The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)₄PF₆] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.

Key words

diazo compounds - α-diazophosphonates - 1,2-hydride migration - tetrakis(acetonitrile)copper(I) hexafluorophosphate - β-amino (E)-enylphosphonates

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