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Enantioselective Construction of Bispirooxindoles via Squaramide‐Catalysed Cascade Michael/Cyclization Reaction
Author(s) -
Zhao BoLiang,
Lin Ye,
Du DaMing
Publication year - 2019
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.201900358
Subject(s) - squaramide , stereocenter , enantioselective synthesis , bifunctional , chemistry , michael reaction , cascade reaction , cascade , organocatalysis , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , chromatography
A series of readily available 2‐(2‐oxoindolin‐3‐yl)malononitriles bearing multiple active sites were first used in asymmetric catalytic synthesis, which have been successfully applied to develop a bifunctional squaramide‐catalyzed cascade Michael/cyclization reaction strategy. Various cyclopentene‐bispirooxindoles with three continuous stereocenters, two of which are quaternary spiro‐stereocenters, were constructed in good yields with excellent stereoselectivities (up to >20:1 dr, >99% ee).