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Copper‐Catalyzed Addition of Grignard Reagents to in situ Generated Indole‐Derived Vinylogous Imines
Author(s) -
Ge Luo,
Zurro Mercedes,
Harutyunyan Syuzanna R.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004232
Subject(s) - indole test , phosphoramidite , chemistry , imine , catalysis , reagent , in situ , enantiomer , combinatorial chemistry , enantioselective synthesis , conjugate , sulfonyl , alkyl , copper , organic chemistry , dna , mathematical analysis , biochemistry , mathematics , oligonucleotide
Chiral indole derivatives are ubiquitous motifs in pharmaceuticals and alkaloids. Herein, the first protocol for catalytic asymmetric conjugate addition of Grignard reagents to various sulfonyl indoles, offering a straightforward approach for the synthesis of chiral 3‐sec‐alkyl‐substituted indoles in high yields and enantiomeric ratios is presented. This methodology makes use of a chiral catalyst based on copper phosphoramidite complexes and in situ formation of vinylogous imine intermediates.