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Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones.
Org Lett. 2006 Nov 23; 8(24):5657-60.OL

Abstract

Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)2X), Rh(COD)2SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents. [reaction: see text].

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Authors+Show Affiliations

Han SB
University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, USA.
Krische MJ
No affiliation info available

MeSH

AldehydesCatalysisCationsKetonesOxidation-ReductionPressureRhodiumStereoisomerismTemperatureVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

17107096

Citation

Han, Soo Bong, and Michael J. Krische. "Reductive Aldol Coupling of Divinyl Ketones Via Rhodium-catalyzed Hydrogenation: Syn-diastereoselective Construction of Beta-hydroxyenones." Organic Letters, vol. 8, no. 24, 2006, pp. 5657-60.
Han SB, Krische MJ. Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones. Org Lett. 2006;8(24):5657-60.
Han, S. B., & Krische, M. J. (2006). Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones. Organic Letters, 8(24), 5657-60.
Han SB, Krische MJ. Reductive Aldol Coupling of Divinyl Ketones Via Rhodium-catalyzed Hydrogenation: Syn-diastereoselective Construction of Beta-hydroxyenones. Org Lett. 2006 Nov 23;8(24):5657-60. PubMed PMID: 17107096.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: syn-diastereoselective construction of beta-hydroxyenones. AU - Han,Soo Bong, AU - Krische,Michael J, PY - 2006/11/17/pubmed PY - 2007/9/22/medline PY - 2006/11/17/entrez SP - 5657 EP - 60 JF - Organic letters JO - Org Lett VL - 8 IS - 24 N2 - Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)2X), Rh(COD)2SbF6 is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents. [reaction: see text]. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17107096/Reductive_aldol_coupling_of_divinyl_ketones_via_rhodium_catalyzed_hydrogenation:_syn_diastereoselective_construction_of_beta_hydroxyenones_ L2 - https://doi.org/10.1021/ol0624023 DB - PRIME DP - Unbound Medicine ER -