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We also attempted to prepare tertiary amide-based auxiliaries for macrocyclization. However, the synthesis of the corresponding amides from N-ethyl-2,3,4,5,6-pentafluorobenzylamine was problematic. Typical peptide couplings (EDC, DCC, HOBt) as well as various reactions involving acyl chlorides failed to afford the desired tertiary amides.
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We also attempted to prepare tertiary amide-based auxiliaries for macrocyclization. However, the synthesis of the corresponding amides from N-ethyl-2,3,4,5,6-pentafluorobenzylamine was problematic. Typical peptide couplings (EDC, DCC, HOBt) as well as various reactions involving acyl chlorides failed to afford the desired tertiary amides.
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48
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55049084774
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3,5-Bis(trifluoromethyl)benzylamine, 80%, Aldrich #26330-1 g, $25.60 US.
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3,5-Bis(trifluoromethyl)benzylamine, 80%, Aldrich #26330-1 g, $25.60 US.
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Although the model systems in our molecular modelling study contain two olefinic sidechains, we believe it is reasonable to assume that similar energetic values would be obtained for en-yne substrates. This based upon the fact that the substitution of an alkyne for a alkene is a minor structural change unlikely to alter the solution state conformations in a significant manner
-
Although the model systems in our molecular modelling study contain two olefinic sidechains, we believe it is reasonable to assume that similar energetic values would be obtained for en-yne substrates. This based upon the fact that the substitution of an alkyne for a alkene is a minor structural change unlikely to alter the solution state conformations in a significant manner.
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The [12]paracyclophane isolated is the endo-product resulting from en-yne metathesis. The corresponding exo-product is never observed, as it results in the formation of a [11]paracyclophane that is too rigid to form via olefin metathesis.
-
The [12]paracyclophane isolated is the endo-product resulting from en-yne metathesis. The corresponding exo-product is never observed, as it results in the formation of a [11]paracyclophane that is too rigid to form via olefin metathesis.
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