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2005
Pyrrole derivatives
R 0120
Silver-Catalyzed Hydroamination: Synthesis of N-Bridgehead Pyrroles, Incorpoa Protection-Deprotection Strategy for Preparation of Cyclic Secondary
22- 106 rating
Vinylogous Carbamates. — A mild and efficient method for the preparation of secondary cyclic vinylogous carbamates (IV) using Eschenmoser sulfide contraction is
developed. The products are rapidly converted into the corresponding N-bridgehead
pyrroles (VII) using a two-step sequence. It involves C-propargylation followed by a
silver-catalyzed intramolecular microwave-assisted hydroamination. The procedure
shows an improvement in overall yields compared to the one-pot approach with the
added bonus that the hydroamination is catalytic with respect to silver(I) whereas the
one-pot procedure requires a stoichiometric equivalent. — (ROBINSON, R. S.;
DOVEY*, M. C.; GRAVESTOCK, D.; Eur. J. Org. Chem. 2005, 3, 505-511; Warren
Res. Lab., Sch. Chem., Univ. KwaZulu-Natal, Scottsville 3209, S. Afr.; Eng.) —
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