Publication: Reaction of gamma-Hydroxy-N-[1-(dimethylcarbamoyl)ethyl]butanamides under the ‘Direct Amide Cyclization’ Conditions
Reaction of gamma-Hydroxy-N-[1-(dimethylcarbamoyl)ethyl]butanamides under the ‘Direct Amide Cyclization’ Conditions
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Iliev, B., Linden, A., & Heimgartner, H. (2006). Reaction of gamma-Hydroxy-N-[1-(dimethylcarbamoyl)ethyl]butanamides under the ‘Direct Amide Cyclization’ Conditions. Helvetica Chimica Acta, 89(1), 153–175. https://doi.org/10.1002/hlca.200690008
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The preparation of the title compounds was achieved via the ‘azirine/oxazolone method’ starting from the corresponding gamma-hydroxy acids. Upon subjecting the gamma-hydroxy-N-[1-(dimethylcarbamoyl)- ethyl]butanamides 4 to the so-called ‘direct amide cyclization’ (DAC) conditions, chlorinated acids 11 or imino lactones 12 were obtained as the sole products instead of the expected cyclodepsipeptides A or their cyclodimers (Scheme 4). Variation of the substituents in 4 did not affect the outcome of the reaction and a mechanism for the f
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- Iliev, Boyan
- Heimgartner, Heinz
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Iliev, B., Linden, A., & Heimgartner, H. (2006). Reaction of gamma-Hydroxy-N-[1-(dimethylcarbamoyl)ethyl]butanamides under the ‘Direct Amide Cyclization’ Conditions. Helvetica Chimica Acta, 89(1), 153–175. https://doi.org/10.1002/hlca.200690008
