Publication: Diazo-transfer reaction with diphenyl phosphorazidate
Diazo-transfer reaction with diphenyl phosphorazidate
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Villalgordo, J. M., Enderli, A., Linden, A., & Heimgartner, H. (1995). Diazo-transfer reaction with diphenyl phosphorazidate. Helvetica Chimica Acta, 78, 1983–1998. https://doi.org/10.1002/hlca.19950780807
Abstract
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Abstract
Diphenyl phosphorazidate (DPPA) was used as the azide source in a one-pot synthesis of 2,2-disubstituted 3-amino-2H-azirines 1 (Scheme 1). The reaction with lithium enolates of amides of type 2, bearing two substituents at C(2), proceeded smoothly in THF at 0°; keteniminium azides C and azidoenamines D are likely intermediates. Under analogous reaction conditions, DPPA and amides of type 3 with only one substituent at C(2) gave 2-diazoamides 5 in fair-to-good yield (Scheme 2). The corresponding 2-diazo derivatives 6-8 were formed in l
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- Villalgordo, Jose M
- Enderli, Adelheid
- Heimgartner, Heinz
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Villalgordo, J. M., Enderli, A., Linden, A., & Heimgartner, H. (1995). Diazo-transfer reaction with diphenyl phosphorazidate. Helvetica Chimica Acta, 78, 1983–1998. https://doi.org/10.1002/hlca.19950780807
