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- Title
Catalytic Asymmetric Synthesis of 3-Indolyl Methanamines Using Unprotected Indoles and N-Boc Imines under Basic Conditions.
- Authors
Arai, Takayoshi; Kakino, Junki
- 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.
- Subjects
CATALYTIC activity; ADDITION reactions; CHEMICAL synthesis; NUCLEOPHILIC reactions; FRIEDEL-Crafts reaction; NUCLEOPHILIC addition (Chemistry)
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 49, p15263
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201607679