Catalytic Asymmetric Synthesis of 3‐Indolyl Methanamines Using Unprotected Indoles and N‐Boc Imines under Basic Conditions |
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| Authors: | Prof?Dr Takayoshi Arai Junki Kakino |
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| Affiliation: | Molecular Chirality Research Center, Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, Chiba, Japan |
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| Abstract: | 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 K2CO3 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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| Keywords: | asymmetric catalysis imines indole ligands palladium |
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