Atroposelective construction of axially chiral enamides via N -allylic alkylation

Herein, we report the catalytic asymmetric synthesis of a unique family of axially chiral enamides in good yields with excellent enantioselectivities under mild conditions. These new axially chiral compounds feature a flexible skeleton and a high degree of rotational freedom, which raises difficulti...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 58; no. 30; pp. 4727 - 4730
Main Authors Zhou, Qian-Yi, Li, Xin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.04.2022
Royal Society of Chemistry
Subjects
Alkylation
Catalysis
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoisomerism
stereoselective synthesis
Stereoselectivity
ATROPISOMERS
ROTATION
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
BARRIER
NONBIARYL
ACCESS
RATIONAL DESIGN
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Summary:Herein, we report the catalytic asymmetric synthesis of a unique family of axially chiral enamides in good yields with excellent enantioselectivities under mild conditions. These new axially chiral compounds feature a flexible skeleton and a high degree of rotational freedom, which raises difficulties for enantiocontrol. A mechanism model is proposed to interpret the stereoselectivity, in which both the steric difference of the ortho substituents and the π–π stacking interaction may contribute to the stereo-control.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D2CC01000C