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Catalytic Asymmetric Synthesis of 3-Indolyl Methanamines Using Unprotected Indoles and N-Boc Imines under Basic Conditions.

Angewandte Chemie 2016 December 6
A chiral imidazolidine-containing NCN/Pd-OTf catalyst (C4) promoted the nucleophilic addition of unprotected indoles to N-Boc imines. Using sulfinyl amines as the N-Boc imine precursors, the combined use of C4 with K2 CO3 activated the NH indoles to give chiral 3-indolyl methanamines with up to 98 % ee. Compared with conventional acid-catalyzed Friedel-Crafts reactions, this reaction proceeds under mildly basic conditions and is advantageous for the use of acid-sensitive substrates.

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