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Lewis‐Acid‐Catalysed Reaction of 3‐Hydroxy‐2‐oxindoles with Terminal Alkynes: Synthetic Approaches to the Pyrroloindoline Alkaloids
Author(s) -
Kinthada Lakshmana K.,
Babu K. Naresh,
Padhi Dikshaa,
Bisai Alakesh
Publication year - 2017
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.201700507
Subject(s) - chemistry , alkyne , lewis acids and bases , alkylation , aryl , alkyl , quaternary carbon , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis
Lewis‐acid‐catalysed reaction of 3‐hydroxy‐2‐oxindoles with a variety of terminal alkynes has been developed. The key step involves alkylation of 3‐aryl (or) 3‐alkyl, 3‐hydroxyoxindoles with terminal alkyne as π‐electron‐rich system to give a variety of 2‐oxindoles with an all‐carbon quaternary centre. On further extension of this method, a variety of spiro‐2‐oxindoles have been synthesized in high yields. The aforementioned methodology has been used in addressing the cyclotryptamine alkaloids linked with aryl group at the pseudobenzylic position.