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Asymmetric Synthesis of Spirooxindoles with Seven Stereocenters via Organocatalyzed One‐pot Three‐component Sequential Cascade Reactions
Author(s) -
Zhao BoLiang,
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.201900218
Subject(s) - stereocenter , squaramide , bifunctional , chemistry , enantioselective synthesis , cascade , cascade reaction , organocatalysis , component (thermodynamics) , michael reaction , combinatorial chemistry , organic chemistry , catalysis , chromatography , physics , thermodynamics
A bifunctional squaramide‐catalyzed one‐pot three‐component Michael/Mannich‐Michael/cyclization sequential cascade reaction for the construction of bispirooxindole‐spirooxindoles was developed in good yields with excellent stereoselectivities (up to >20:1 dr, 99% ee). A series of original cinnamoyl‐3‐ylideneoxindoles have been applied to this sequential cascade strategy for the first time. This new strategy provides a process for the enantioselective construction of bispirooxindole‐spirooxindoles with seven stereocenters, of which three are quaternary spiro‐stereocenters.