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Organocatalytic Morita–Baylis–Hillman/Michael/Acetalization Cascade: Procedure‐Controlled Diastereodivergence in the Asymmetric Synthesis of Fully Substituted Tetrahydropyrans
Author(s) -
Han Bo,
Xie Xin,
Huang Wei,
Li Xiang,
Yang Lei,
Peng Cheng
Publication year - 2014
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.201400622
Subject(s) - chemistry , kinetic resolution , enantioselective synthesis , cascade , organocatalysis , catalysis , combinatorial chemistry , cascade reaction , sequence (biology) , stereochemistry , organic chemistry , biochemistry , chromatography
Modulating the diastereoselectivity of stereochemically complex molecules in asymmetric synthesis remains a challenge, especially when the reaction cycle produces no net change in the catalysts, ligands, substrates or additives. Here we accomplish a controlled diastereodivergence in the asymmetric synthesis of fully functionalized tetrahydropyrans by adjusting the sequence of an organocatalytic cascade reaction. We also show that this one‐pot operation provides two synthetically important architectures with excellent stereocontrol. To the best of our knowledge, this is the first published kinetic resolution of MBH alcohols in an organocascade.