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Selective binding of one enantioface of monosubstituted alkenes to the chiral transition metal Lewis acid [(.eta.5-C5H5)Re(NO)(PPh3)]+

Cite this: J. Am. Chem. Soc. 1988, 110, 12, 4082–4084
Publication Date (Print):June 1, 1988
https://doi.org/10.1021/ja00220a082
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Cited By

This article is cited by 19 publications.

  1. Ke Zhang, Charles B. Musgrave III, Diane A. Dickie, William A. Goddard III, T. Brent Gunnoe. Capping Arene Ligated Rhodium-Catalyzed Olefin Hydrogenation: A Model Study of the Ligand Influence on a Catalytic Process That Incorporates Oxidative Addition and Reductive Elimination. Organometallics 2022, 41 (22) , 3373-3386. https://doi.org/10.1021/acs.organomet.2c00317
  2. Steven J. Dakermanji, Karl S. Westendorff, Emmit K. Pert, Katy B. Wilson, Jeffery T. Myers, Justin H. Wilde, Diane A. Dickie, Kevin D. Welch, W. Dean Harman. Spatial Recognition Within Terpenes: Redox and H-bond Promoted Linkage Isomerizations and the Selective Binding of Complex Alkenes. Organometallics 2020, 39 (10) , 1961-1975. https://doi.org/10.1021/acs.organomet.0c00151
  3. Michael B. Wells,, Jonathan E. McConathy,, Peter S. White, and, Joseph L. Templeton. Regioselective and Stereoselective Reactions of 2-Butyne Bound to a Resolved Chiral Tungsten(II) Center. Organometallics 2002, 21 (23) , 5007-5020. https://doi.org/10.1021/om020416g
  4. T. Brent Gunnoe,, Michal Sabat, and, W. Dean Harman. Stereoselective Dihapto-Binding of Prochiral Aromatic Compounds by {TpRe(CO)(PMe3)}:  Synthesis, Characterization, Stability, and Enantiofacial Discrimination (Tp = Hydrido(tris)pyrazolylborate). Organometallics 2000, 19 (5) , 728-740. https://doi.org/10.1021/om9906722
  5. Lisa E. Helberg,, T. Brent Gunnoe,, Benjamin C. Brooks,, Michal Sabat, and, W. Dean Harman. Rhenium(I) Terpyridine π-Bases:  Reversible η2-Coordination of Ketones, Aldehydes, and Olefins in the Terpyridine Plane. Organometallics 1999, 18 (4) , 573-581. https://doi.org/10.1021/om980500p
  6. Andreas Böhm, Henri Brunner, Wolfgang Beck. Chirale Halbsandwich-Pentamethylcyclopentadienyl-Rhodium(III)- und Iridium(III)-Komplexe mit Schiff-Basen aus Salicylaldehyd und α-Aminosäureestern [1]. Zeitschrift für anorganische und allgemeine Chemie 2008, 634 (2) , 274-278. https://doi.org/10.1002/zaac.200700388
  7. Pradeep Gutta, Dean J. Tantillo. Theoretical Studies on Farnesyl Cation Cyclization:  Pathways to Pentalenene. Journal of the American Chemical Society 2006, 128 (18) , 6172-6179. https://doi.org/10.1021/ja058031n
  8. Tang-Sheng Peng, Atta M. Arif, John A. Gladysz. Thermodynamic Enantioface-Binding Selectivities of Monosubstituted Alkenes to a Highly Discriminating Chiral Transition -MetalLewis Acid; equilibration of diastereoisomeric (cyclopentadienyl)(alkene)(nitrosyl)(triphenylphosphine)rhenium complexes ([Re(?5-C5H5)(CH2 = CHR)(NO) (PPh3)]+BF4?). Helvetica Chimica Acta 1992, 75 (2) , 442-456. https://doi.org/10.1002/hlca.19920750204
  9. David J. Ager, Michael B. East. Methodology to establish 1,2- and 1,3-difunctionality for the synthesis of carbohydrate derivates. Tetrahedron 1992, 48 (14) , 2803-2894. https://doi.org/10.1016/S0040-4020(01)90970-6
  10. Bernard W. Rockett, George Marr. Organic reactions of selected π-complexes annual survey covering the year 1988. Journal of Organometallic Chemistry 1990, 392 (1-3) , 161-283. https://doi.org/10.1016/0022-328X(90)80192-3
  11. Ulrich Kölle, Janusz Kossakowski, Gerhard Raabe. Cp*Ru(acac) — ein koordinativ ungesättigter, stabiler 16-Valenzelektronen-Komplex. Angewandte Chemie 1990, 102 (7) , 839-840. https://doi.org/10.1002/ange.19901020732
  12. Sénamé K. Agbossou, Whitney W. Smith, John A. Gladysz. Synthesis and Reactivity of Chiral Rhenium Alcohol Complexes of the Formula [(η5-C5H5)Re(NO)(PPh3)(ROH)]⊕BF4⊖. Chemische Berichte 1990, 123 (6) , 1293-1299. https://doi.org/10.1002/cber.19901230612
  13. Michael A. Dewey, Atta M. Arif, J.A. Gladysz. Syntheses and structures of σ-pyridine, quinoline, and isoquinoline complexes of the formula [(η5-C5H5)Re(NO)(PPh3)(NCxHy)]+ CF3SO3−. Journal of Organometallic Chemistry 1990, 384 (1-2) , C29-C32. https://doi.org/10.1016/0022-328X(90)87079-S
  14. David N.A. Fox, Timothy Gallagher. Asymmetric synthesis via electrophile-mediated cyclisations. Tetrahedron 1990, 46 (13-14) , 4697-4710. https://doi.org/10.1016/S0040-4020(01)85590-3
  15. Tang-Sheng Peng, J.A. Gladysz. Regiospecific, diastereospecific and enantiospecific nucleophilic additions to chiral monosubstituted alkene complexes of the formula [(η5-C5H5)Re(NO)(PPh3)(H2CCHR)]+ BF4−. Tetrahedron Letters 1990, 31 (31) , 4417-4420. https://doi.org/10.1016/S0040-4039(00)97636-6
  16. Tang-Sheng Peng, J. A. Gladysz. Isomerization of diastereoisomeric alkene complexes of the formula [(η 5 -C 5 H 5 )Re(NO)(PPh 3 )(H 2 CCHR)] + ; the alkene enantioface bound to the metal can ‘flip’ without alkene dissociation. J. Chem. Soc., Chem. Commun. 1990, 110 (13) , 902-903. https://doi.org/10.1039/C39900000902
  17. . Organische Chemie 1988. Nachrichten aus Chemie, Technik und Laboratorium 1989, 126-142. https://doi.org/10.1002/nadc.19890370206
  18. Charles M. Garner, Jesus M. Fernández, J.A. Gladysz. Stereoselective addition of cyanide ion to chiral rhenium π-aldehyde complexes of the formulae [(η5-C5H5)Re(NO)(PPh3)(η2-OCHR)]+ BF4−. Tetrahedron Letters 1989, 30 (30) , 3931-3934. https://doi.org/10.1016/S0040-4039(00)99287-6
  19. G. S. BODNER, J. M. FERNANDEZ, A. M. ARIF, J. A. GLADYSZ. ChemInform Abstract: Selective Binding of One Enantioface of Monosubstituted Alkenes to the Chiral Transition Metal Lewis Acid ((η5-C5H5)Re(NO)(PPh3))+.. ChemInform 1988, 19 (40) https://doi.org/10.1002/chin.198840221

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