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Brønsted Acid Promoted Regioselective C‐3 Arylation and Heteroarylation of Spiro‐epoxyoxindoles for the Construction of All Carbon Quaternary Centres: A Detailed Study
Author(s) -
Hajra Saumen,
Maity Subrata,
Roy Sayan,
Maity Ramkrishna,
Samanta Srikrishna
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801524
Subject(s) - regioselectivity , chemistry , indole test , quaternary carbon , brønsted–lowry acid–base theory , ring (chemistry) , intermolecular force , solvent , combinatorial chemistry , catalysis , friedel–crafts reaction , carbon fibers , organic chemistry , medicinal chemistry , molecule , enantioselective synthesis , materials science , composite number , composite material
An efficient strategy for the synthesis of all carbon quaternary centres has been developed via Brønsted acid‐promoted highly regioselective intermolecular Friedel–Crafts reactions of heteroarenes or arenes with spiro‐epoxyoxindoles. In addition, we have successfully performed the ring opening reaction in relatively cheap condition using water as a solvent. Beneficially, we have utilized the methodology as the key step for the synthesis of advanced precursors of various natural and unnatural indole alkaloids.