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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Cu(I)-catalyzed asymmetric diamination of conjugated dienes
Haifeng Du1, Baoguo Zhao, Weicheng Yuan
1Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Abstract:
A Cu(I)-catalyzed asymmetric diamination for a variety of conjugated dienes and a triene with encouraging ee's has been effectively achieved using (R)-DTBM-SEGPHOS as a chiral ligand and di- tert-butyldiaziridinone as the nitrogen source.
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Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
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Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...

