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Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine.
Org Lett. 2006 Feb 02; 8(3):519-22.OL

Abstract

[reaction: see text]. Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions.

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Authors+Show Affiliations

Jung CK
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Garner SA
No affiliation info available
Krische MJ
No affiliation info available

MeSH

AldehydesCatalysisHydrogenationKetonesMolecular StructurePhosphinesRhodiumStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16435874

Citation

Jung, Cheol-Kyu, et al. "Hydrogen-mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed By Rhodium: High Syn-selectivity Through the Effect of Tri-2-furylphosphine." Organic Letters, vol. 8, no. 3, 2006, pp. 519-22.
Jung CK, Garner SA, Krische MJ. Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. Org Lett. 2006;8(3):519-22.
Jung, C. K., Garner, S. A., & Krische, M. J. (2006). Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. Organic Letters, 8(3), 519-22.
Jung CK, Garner SA, Krische MJ. Hydrogen-mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed By Rhodium: High Syn-selectivity Through the Effect of Tri-2-furylphosphine. Org Lett. 2006 Feb 2;8(3):519-22. PubMed PMID: 16435874.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrogen-mediated aldol reductive coupling of vinyl ketones catalyzed by rhodium: high syn-selectivity through the effect of tri-2-furylphosphine. AU - Jung,Cheol-Kyu, AU - Garner,Susan A, AU - Krische,Michael J, PY - 2006/1/27/pubmed PY - 2006/10/19/medline PY - 2006/1/27/entrez SP - 519 EP - 22 JF - Organic letters JO - Org Lett VL - 8 IS - 3 N2 - [reaction: see text]. Catalytic hydrogenation of methyl vinyl ketone (MVK) and ethyl vinyl ketone (EVK) in the presence of diverse aldehydes at ambient temperature and pressure using tri-2-furylphosphine-ligated rhodium catalysts enables formation of aldol products with high levels of syn-diastereoselectivity. A progressive increase in diastereoselectivity is observed upon sequential replacement of phenyl residues for 2-furyl residues (Ph3P, FurPh2P, Fur2PhP, Fur3P). Hydrogen-labile functional groups, including alkynes, alkenes, benzylic ethers, and nitroarenes, remain intact under the coupling conditions. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16435874/Hydrogen_mediated_aldol_reductive_coupling_of_vinyl_ketones_catalyzed_by_rhodium:_high_syn_selectivity_through_the_effect_of_tri_2_furylphosphine_ L2 - https://doi.org/10.1021/ol052859x DB - PRIME DP - Unbound Medicine ER -