Ligand-Dependent Regiodivergent Enantioselective Allylic Alkylations of α‑Trifluoromethylated Ketones

The asymmetric introduction of the CF3 unit is a powerful tool for modifying pharmacokinetic properties and slowing metabolic degradation in medicinal chemistry. A catalytic and enantioselective addition of α-CF3 enolates allows for expeditious access to functionalized chiral building blocks with CF...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 7; pp. 2443 - 2448
Main Authors Zhu, Yi, Ni, Yifan, Lu, Chenxi, Wang, Xiaochen, Wang, Yi, Xue, Xiao-Song, Pan, Yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.04.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALDOL
REAGENTS
ALLYLATION
DIRECT GENERATION
FLUORINATION
MBH CARBONATES
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Summary:The asymmetric introduction of the CF3 unit is a powerful tool for modifying pharmacokinetic properties and slowing metabolic degradation in medicinal chemistry. A catalytic and enantioselective addition of α-CF3 enolates allows for expeditious access to functionalized chiral building blocks with CF3-containing stereogenicity. The computational studies reveal that the choice of ligand in a designed palladium-complex system regulates the regioselectivity and stereoselectivity of the asymmetric allylic alkyation of α-CF3 ketones and Morita–Baylis–Hillman adducts.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00329