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N-Boc-dienylamine 2g has been recovered with an unsatisfactory yield (25%, entry 7, Table 1) along with byproducts coming from the damage of the Boc protecting group, which turns out to be unstable under superbasic conditions. N-Protected alkyl imines have not been considered for this work, as they enolize in the superbasic medium.
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N-Boc-dienylamine 2g has been recovered with an unsatisfactory yield (25%, entry 7, Table 1) along with byproducts coming from the damage of the Boc protecting group, which turns out to be unstable under superbasic conditions. N-Protected alkyl imines have not been considered for this work, as they enolize in the superbasic medium.
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Enantioselective α-arylglycine synthesis is currently under investigation in our laboratory.
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Enantioselective (α-arylglycine synthesis is currently under investigation in our laboratory.
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We decided to consider only N-tosyldienylamines on the grounds that less nucleophilic nitrogen atoms are more reactive in aminopalladation reactions. For examples on this subject, see
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We decided to consider only N-tosyldienylamines on the grounds that less nucleophilic nitrogen atoms are more reactive in aminopalladation reactions. For examples on this subject, see: Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
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Attempts to reduce the amount of Pd(II) by the presence of Cu(II) salts as cocatalysts led to low yield of pyrroles.
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Attempts to reduce the amount of Pd(II) by the presence of Cu(II) salts as cocatalysts led to low yield of pyrroles.
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