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Organocatalytic Tandem Reaction to Construct Six‐Membered Spirocyclic Oxindoles with Multiple Chiral Centres through a Formal [2+2+2] Annulation
Author(s) -
Jiang Kun,
Jia ZhiJun,
Chen Shi,
Wu Li,
Chen YingChun
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903009
Subject(s) - annulation , stereocenter , oxindole , tandem , electrophile , chemistry , stereoselectivity , cascade reaction , stereochemistry , michael reaction , amine gas treating , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , composite material
An efficient tandem reaction for the asymmetric synthesis of six‐membered spirocyclic oxindoles has been successfully developed through a formal [2+2+2] annulation strategy. The amine‐catalysed stereoselective Michael addition of aliphatic aldehydes to electron‐deficient olefinic oxindole motifs gave chiral C3 components, which were further combined with diverse electrophiles (activated olefins or imines) to afford spirocyclic oxindoles with versatile molecular complexity (up to six contiguous stereogenic centres, high diastereo‐ and enantioselectivities).