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- Title
Organocatalytic Morita-Baylis-Hillman/Michael/Acetalization Cascade: Procedure-Controlled Diastereodivergence in the Asymmetric Synthesis of Fully Substituted Tetrahydropyrans.
- Authors
Han, Bo; Xie, Xin; Huang, Wei; Li, Xiang; Yang, Lei; Peng, Cheng
- Abstract
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.
- Subjects
ASYMMETRIC synthesis; TETRAHYDROPYRANYL compounds synthesis; ORGANOCATALYSIS; KINETIC resolution; CHEMICAL reactions
- Publication
Advanced Synthesis & Catalysis, 2014, Vol 356, Issue 17, p3676
- ISSN
1615-4150
- Publication type
Other
- DOI
10.1002/adsc.201400622