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The opposite regiochemical outcome in the Ag-catalyzed (controlled by the sulfonyl group) and Cu-catalyzed cycloaddition (controlled by the acetyl group) could be due, at least in part, to the highly oxophilic nature of the copper Lewis acids, which would tend to reinforce the carbonyl regiochemical control
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The opposite regiochemical outcome in the Ag-catalyzed (controlled by the sulfonyl group) and Cu-catalyzed cycloaddition (controlled by the acetyl group) could be due, at least in part, to the highly oxophilic nature of the copper Lewis acids, which would tend to reinforce the carbonyl regiochemical control.
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Regioisomer 10 a can be separated by standard silica gel chromatography, isolated as a single diastereoisomer. For the regiochemical and stereochemical assignment of isomers 8 a and 10 a, see the Supporting Information
-
Regioisomer 10 a can be separated by standard silica gel chromatography, isolated as a single diastereoisomer. For the regiochemical and stereochemical assignment of isomers 8 a and 10 a, see the Supporting Information.
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Some interesting types of pyrrole-based natural products, such as prodigiosins and marineosins, present an electronically rich substitution at C-3 in the pyrrole unit
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Some interesting types of pyrrole-based natural products, such as prodigiosins and marineosins, present an electronically rich substitution at C-3 in the pyrrole unit.
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2, 4 Å molecular sieves, RT, 5 h; then DBU, RT, 30 min. (Figure Presented)
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