PyBidine/copper catalyst: asymmetric exo'-selective [3+2] cycloaddition using imino ester and electrophilic indole
1Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage-ku, Chiba 263-8522 (Japan) http://synthesis.chem.chiba-u.jp/index.htm.
Abstract:
Electrophilic indoles having two electron-withdrawing groups undergo nucleophilic attack at C2 and electrophilic functionalization at C3. This is the first enantioselective formal [3+2] cycloaddition using electrophilic indoles. The PyBidine/Cu catalyst smoothly promoted highly enantio- and exo'-selective [3+2] cycloaddition using imino esters and 3-nitroindoles. This reaction provides a method for the preparation of diverse and complex chiral pyrroloindoline compounds.
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