Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 6, Pages 1309-1316Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901380
Keywords
Solvent-mediated; C3/C7 alkylation; Indoles; Enantioselectivity; Regioselectivity switch
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Funding
- National Natural Science Foundation of China [21772199, 21971264]
- Research Foundation for Advanced Talents of Sun Yat-sen University [36000-18821101]
- Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery [2019B030301005]
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The first solvent-mediated tunable C3/C7 regio- and enantioselective Friedel-Crafts alkylation of 4-aminoindoles with alpha-ketimino esters has been developed. This catalysis allows the highly regioselective formation of indole C3 and C7 alkylation products, both in high yields (up to 96%) and excellent enantioselectivities (up to 99% ee). Mechanism study revealed that the hydrogen-bonding interactions of the solvents with the catalyst played a vital role for the regioselectivity switch. Furthermore, the corresponding products are indole containing unnatural alpha-amino acid derivatives bearing a quaternary stereocenter and enable many further elaborations.
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