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- Title
Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine.
- Authors
Kano, Taichi; Sugimoto, Hisashi; Maruyama, Hiroki; Maruoka, Keiji
- 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.
- Subjects
CONJUGATE addition reactions; ALDEHYDES; COPPER catalysts; ELECTRON-deficient compounds; CARBON-carbon bonds
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 29, p8462
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201500225