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Catalytic Asymmetric Synthesis of 3‐Indolyl Methanamines Using Unprotected Indoles and N‐Boc Imines under Basic Conditions
Author(s) -
Arai Takayoshi,
Kakino Junki
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201607679
Subject(s) - catalysis , chemistry , imine , imidazolidine , friedel–crafts reaction , reaction conditions , nucleophile , combinatorial chemistry , nucleophilic addition , organic chemistry , medicinal chemistry
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 K 2 CO 3 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.