title: Asymmetric synthesis of fully substituted cyclopentane-oxindoles through an organocatalytic triple Michael domino reaction.
abstract: An efficient, highly stereoselective asymmetric synthesis of fully functionalized cyclopentanes bearing an oxindole moiety and several other functional groups in one pot has been developed. Key step is an organocatalytic triple Michael domino reaction forming three C-C bonds and six stereocenters, including a quaternary one. Starting from equimolar amounts of simple substrates, a high molecular complexity can be reached after a Wittig olefination in one pot. The new protocol can easily be scaled up to gram amounts.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
authors.forename: Liang-Hua
authors.initials: LH
authors.lastname: Zou
authors.forename: Arne R
authors.initials: AR
authors.lastname: Philipps
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008968:Molecular Conformation; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole
keywords: asymmetric synthesis; cyclopentanes; domino reactions; organocatalysis; oxindoles