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The Application of N‐Protected 3‐Vinylindoles in Chiral Phosphoric Acid‐Catalyzed [3+2] Cyclization with 3‐Indolylmethanols: Monoactivation of the Catalyst to Vinyliminium
Author(s) -
Fan Tao,
Zhang HongHao,
Li Can,
Shen Yang,
Shi Feng
Publication year - 2016
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.201501175
Subject(s) - enantioselective synthesis , chemistry , moiety , phosphoric acid , indole test , catalysis , isatin , combinatorial chemistry , organocatalysis , stereochemistry , organic chemistry
A highly enantioselective [3+2] cyclization of 3‐vinylindoles with isatin‐derived 3‐indolylmethanols has been established in the presence of chiral phosphoric acid, which constructed the enantioenriched cyclopenta[ b ]indole scaffold linking a 3‐vinylindole moiety in generally good yields, considerable diastereoselectivities and high enantioselectivities (up to 93%, >95:5 dr , >99.5:0.5 er ). More importantly, this reaction utilized N‐protected 3‐vinylindoles as competent reactants, which confronted the challenge in realizing a successful monoactivation mode of chiral phosphoric acid to vinyliminium in 3‐indolylmethanol‐involved enantioselective transformations. Besides, this protocol also settled the challenge in realizing a highly enantioselective [3+2] cyclization of 3‐vinylindoles with 3‐indolylmethanols, which would serve as a useful strategy for constructing an enantioenriched cyclopenta[ b ]indole scaffold linking a 3‐vinylindole moiety.