Palladium-Catalyzed Nucleophilic Reaction of Alkylidenecyclopropanes with β,γ-Unsaturated α‑Ketoesters: Ligand-Controlled Divergent Synthesis

A palladium-catalyzed ligand-controlled selective 1,4-addition and cycloaddition reaction of β,γ-unsaturated α-ketoesters with alkylidenecyclopropanes (ACPs) has been developed. Using ACPs and β,γ-unsaturated α-ketoesters as starting materials, γ-dienyl-α-ketoesters and dihydro-2H-pyrans could be pr...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 24; no. 36; pp. 6692 - 6696
Main Authors Liu, Xin-Lian, Zhang, You-Ya, Li, Lin, Tan, Lu-Qi, Huang, Yin-Ai, Ma, Ai-Jun, Peng, Jin-Bao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.09.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HETEROCYCLES
METHYLENECYCLOPROPANES
CONSTRUCTION
DIMERIZATION
SULFUR
BOND-CLEAVAGE
CYCLIZATION
ACCESS
Online AccessGet full text

Cover

More Information
Summary:A palladium-catalyzed ligand-controlled selective 1,4-addition and cycloaddition reaction of β,γ-unsaturated α-ketoesters with alkylidenecyclopropanes (ACPs) has been developed. Using ACPs and β,γ-unsaturated α-ketoesters as starting materials, γ-dienyl-α-ketoesters and dihydro-2H-pyrans could be prepared selectively by modulating the ligand. A range of multisubstituted α-ketoesters and dihydro-2H-pyrans were obtained in moderate to excellent yields with excellent regioselectivities.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02839