A Novel Stereocontrolled Synthesis of 1,2-<i>trans</i> Cyclopropyl Ketones via Suzuki-Type Coupling of Acid Chlorides with Cyclopropylboronic Acids

Abstract

[reaction: see text] The palladium-catalyzed cross-coupling reaction of cyclopropylboronic acids with acyl chlorides was achieved by the combination of Ag(2)O and K(2)CO(3) as the base. Highly enantiomerically enriched cyclopropyl ketones (ee >90%) were also obtained by the reaction of corresponding chiral cyclopropylboronic acids.

References

Page 1

	Year	Citations
Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998 Akira Suzuki Journal of Organometallic Chemistry Organoboron DerivativesCross-coupling ReactionEngineeringOrganic ElectrochemistryOrganic Chemistry	1999	2.9K
Dramatic rate enhancement of Suzuki diene synthesis. Its application to palytoxin synthesis Jun’ichi Uenishi, Jean Marie Beau, Robert W. Armstrong, Journal of the American Chemical Society EngineeringHeterocyclicChemometricsSuzuki Diene SynthesisOrganic Chemistry	1987	300
A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids Mustapha Haddach, James R. McCarthy Tetrahedron Letters Arylboronic AcidsCross-coupling ReactionEnantioselective SynthesisEngineeringPalladium-catalyzed Cross-coupling	1999	173
A New Transformation of Silanols. Palladium-Catalyzed Cross-Coupling with Organic Halides in the Presence of Silver(I) Oxide Kazunori Hirabayashi, Jun Kawashima, Yasushi Nishihara, Organic Letters Materials ScienceInorganic ChemistryChemical EngineeringCatalyst SystemEngineering	1999	167
Synthesis of unsymmetric ketones via ligandless Pd-catalyzed reaction of acyl chlorides with organoboranes D. N. Korolev Tetrahedron Letters Chemical EngineeringEnantioselective SynthesisEngineeringCross-coupling ReactionLigandless Pd-catalyzed Reaction	1999	131
Investigations into ambient temperature biaryl coupling reactions James C. Anderson, Craig Roberts Tetrahedron Cross-coupling ReactionEngineeringPhysicsNatural SciencesAmbient Temperature Biaryl	1997	91
Rearrangements of Radical Ions: What It Means To Be Both a Radical <i>and</i> an Ion James M. Tanko, J. Paige Phillips Journal of the American Chemical Society Chemical EngineeringMolecular SciencesEngineeringRadical IonsRadical (Chemistry)	1999	66
Isolation and structure of constanolactones A and B, new cyclopropyl hydroxy-eicosanoids from the temperate red alga constantinea simplex Dale G. Nagle, William H. Gerwick Tetrahedron Letters BiologyConstanolactones ABiosynthesisBioorganic ChemistryEngineering	1990	65
A novel route to cyclopropyl ketones, aldehydes, and carboxylic acids. Karen E. Rodriques Tetrahedron Letters Carboxylic AcidsEngineeringHeterocyclicBiochemistryOrganic Chemistry	1991	40
Stereospecific synthesis of 9-demethylretinoids via palladium-catalyzed vinylboronic acid-vinyl iodide cross coupling Ángel R. de Lera, Alicia Torrado, Beatriz Iglesias, Tetrahedron Letters Cross-coupling ReactionEngineeringStereospecific SynthesisOrganic ChemistryOrganometallic Catalysis	1992	31

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