Journal
CHEMICAL SCIENCE
Volume 10, Issue 32, Pages 7579-7583Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc02431j
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Funding
- National Natural Science Foundation of China [21773051]
- Zhejiang Provincial Natural Science Foundation of China [LY18B020013, LZ18B020001]
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The Sonogashira-type cross-coupling reaction is one of the most significant alkynylation transformations in organic chemistry. However, highly enantioselective alkynylation via the Sonogashira-type cross-coupling reaction is rather limited, mainly due to the difficulties in matching the stereoselective induction of chiral ligands with the combinational behavior of Pd/Cu-based bimetallic catalysts. We herein report novel enantioselective palladium/copper-catalyzed alkyl alkynylation of cyclobutanones with terminal alkynes via tandem C-C bond activation/Sonogashira-type cross coupling reaction, in which a novel chiral TADDOL-derived phosphoramidite ligand bearing fluorine and silicon-based bulky groups simplified as TFSi-Phos is found to be an efficient ligand for both C(sp(2))-C(sp(3)) bond cleavage and new C(sp(3))-C(sp) bond formation. A wide range of chiral alkynylated indanones bearing an all-carbon quaternary stereocenter are obtained efficiently with up to 97.5 : 2.5 er.
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