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Regio‐ and Stereoselective Conjugate Addition of Aldehydes to β‐Tosyl Enones under the Catalysis of a Binaphthyl‐Modified Chiral Amine
Authors:Dr. Taichi Kano  Hisashi Sugimoto  Hiroki Maruyama  Prof. Keiji Maruoka
Affiliation:Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606‐8502 (Japan)
Abstract:A simple axially chiral amine catalyst promoted the regio‐, diastereo‐, and enantioselective conjugate addition of aldehydes to β‐tosyl enones, which serve as ynone surrogates. The adducts were readily converted by treatment with L‐selectride into less accessible enones with a γ stereogenic center. Such compounds cannot be prepared through the amine‐catalyzed conjugate addition of aldehydes to ynones. The obtained enones underwent further conjugate addition of diorganozinc compounds in the presence of a copper catalyst.
Keywords:aldehydes  asymmetric catalysis  Michael addition  olefination  organocatalysis
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