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Organocatalytic Asymmetric Four‐Component [5+1+1+1] Cycloadditions via a Quintuple Cascade Process
Author(s) -
Xiao Wei,
Zhou Zhi,
Yang QianQian,
Du Wei,
Chen YingChun
Publication year - 2018
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.201800636
Subject(s) - knoevenagel condensation , chemistry , michael reaction , component (thermodynamics) , cascade , nucleophile , cycloaddition , combinatorial chemistry , organocatalysis , molecule , methylene , stereochemistry , computational chemistry , organic chemistry , enantioselective synthesis , catalysis , physics , chromatography , thermodynamics
An asymmetric four‐component [5+1+1+1] formal cycloaddition reaction of 3‐substituted 2‐cyclopentenones, activated methylene nucleophiles and two molecules of aldehydes is developed under chiral primary aminocatalysis, producing a diversity of highly enantioenriched fused and spirocyclic frameworks with high molecular complexity. Mechanism studies indicate that the current reaction proceeds in a challenging cascade quintuple Knoevenagel condensation/Michael addition/retro‐Michael addition/Michael addition/Michael addition sequence via diverse aminocatalytic modes.