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Supported Bifunctional Chiral Thioureas as Catalysts in the Synthesis of 3‐Amino‐2‐Oxindoles through Enantioselective aza‐Friedel‐Crafts Reaction: Application in Continuous Flow Processes
Author(s) -
RodríguezRodríguez Marta,
Maestro Alicia,
Andrés José M.,
Pedrosa Rafael
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000238
Subject(s) - chemistry , enantioselective synthesis , bifunctional , friedel–crafts reaction , oxindole , catalysis , isatin , yield (engineering) , organic chemistry , thiourea , organocatalysis , combinatorial chemistry , materials science , metallurgy
Supported cinchone‐derived thioureas promote highly enantioselective aza‐Friedel‐Crafts reaction of different naphthols with a variety of N‐Boc ketimines derived from isatin. The catalysts are recoverable and reusable, and one of the supported catalysts has been used in a flow process allowing the synthesis of 3‐amino‐2‐oxindole derivatives in multigram scale with high yield and enantioselectivity.