4-(Dimethylaminomethyl)phenylacetic acid hydrochloride
CAS Number:
99985-52-1
Molecular Formula:
C11H16ClNO2
Enantio- and diastereoselective conjugate addition of pyridyl alkyl ketones to enones by Cu(ii)-Lewis acid/Brønsted base catalysis
Literature Information
Publication Date
2023-12-06
DOI
10.1039/D3QO01707A
Impact Factor
5.281
Authors
Soojin Kwak, Minhyeok Lee, Eunji Sim, Sarah Yunmi Lee
View Original
Abstract
We report herein a chiral Cu(II)-Lewis acid (LA)/Brønsted base-catalyzed process for the enantio- and diastereoselective conjugate addition of various 2-pyridyl alkyl ketones to β-substituted enones under mild conditions. Acid and base catalysts cooperatively deprotonate an α-proton of pyridyl ketones containing diverse alkyl chains, facilitating the generation of α-pyridyl enolates bound to Cu(II)-LA involving carboxylate ligands. The carboxylate ligands which contain extended alkyl chains such as cyclohexanebutyrates, along with a chiral bisphosphine ligand, play a significant role in stereocontrol, supported by experimental and DFT studies. Cu(II) (Z)-enolate complexes, of which one face is effectively blocked by a carboxylate, react with enones to create the stereogenic carbon–carbon bond in the rate-determining step.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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Molecular Formula:
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