메뉴 건너뛰기




Volumn 72, Issue 4, 2007, Pages 1063-1072

Hydrogen-mediated C-C bond formation: A broad new concept in catalytic C-C coupling

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; ORGANIC COMPOUND;

EID: 33846995439     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061895m     Document Type: Review
Times cited : (159)

References (115)
  • 1
    • 33846978994 scopus 로고    scopus 로고
    • An abbreviated segment of this review has been published previously: Ngai, M.-Y, Krische, M. J. Lessons in Green Chemistry from the Smallest of Molecules, C-C Bond Formation via Catalytic Hydrogenation. Chim. Oggi/Chem. Today 2006, 24 4, 12
    • An abbreviated segment of this review has been published previously: Ngai, M.-Y.; Krische, M. J. Lessons in Green Chemistry from the Smallest of Molecules - C-C Bond Formation via Catalytic Hydrogenation. Chim. Oggi/Chem. Today 2006, 24 (4), 12.
  • 2
    • 33846987035 scopus 로고    scopus 로고
    • Homogeneous Asymmetric Hydrogenation: Mature and Fit for Early Stage Drug Development
    • (a) Thommen, M. Homogeneous Asymmetric Hydrogenation: Mature and Fit for Early Stage Drug Development. Spec. Chem. Mag. 2005, 25, 26.
    • (2005) Spec. Chem. Mag , vol.25 , pp. 26
    • Thommen, M.1
  • 3
    • 25144493102 scopus 로고    scopus 로고
    • Chiral Catalysis
    • (b) Thayer, A. M. Chiral Catalysis. Chem. Eng. News 2005, 83 (36), 40.
    • (2005) Chem. Eng. News , vol.83 , Issue.36 , pp. 40
    • Thayer, A.M.1
  • 4
    • 20444485229 scopus 로고    scopus 로고
    • Krische, M. J. A Brief Perspective on Catalysis from its Origins and at the Threshold of the 21st Century. Tetrahedron 2005, 61, 6169.
    • Krische, M. J. A Brief Perspective on Catalysis from its Origins and at the Threshold of the 21st Century. Tetrahedron 2005, 61, 6169.
  • 5
    • 0026418434 scopus 로고
    • The Atom Economy: A Search for Synthetic Efficiency
    • For reviews, see: a
    • For reviews, see: (a) Trost, B. M. The Atom Economy: A Search for Synthetic Efficiency. Science 1991, 256, 1471.
    • (1991) Science , vol.256 , pp. 1471
    • Trost, B.M.1
  • 6
    • 33750309194 scopus 로고
    • Atom Economy - A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way
    • (b) Trost, B. M. Atom Economy - A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the Way. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
    • (1995) Angew. Chem., Int. Ed. Engl , vol.34 , pp. 259
    • Trost, B.M.1
  • 7
    • 0002466970 scopus 로고
    • Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes
    • Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. Org. Synth. Theor. Appl. 1993, 2, 27.
    • (1993) Org. Synth. Theor. Appl , vol.2 , pp. 27
    • Wender, P.A.1    Miller, B.L.2
  • 9
    • 0347933770 scopus 로고    scopus 로고
    • Catalysis and Pollution Prevention
    • Sheldon, R. Catalysis and Pollution Prevention. Chem. Ind. 1997, 12.
    • (1997) Chem. Ind , pp. 12
    • Sheldon, R.1
  • 11
    • 0037600858 scopus 로고
    • Action of Hydrogen on Acetylene in the Presence of Nickel
    • (b) Sabatier, P.; Senderens. J.-B. Action of Hydrogen on Acetylene in the Presence of Nickel C. R. Hebd. Seances Acad. Sci. 1899, 128, 1173.
    • (1899) C. R. Hebd. Seances Acad. Sci , vol.128 , pp. 1173
    • Sabatier, P.1    Senderens, J.-B.2
  • 12
    • 0008652784 scopus 로고
    • Direct Hydrogenation Realized in the Presence of Reduced Nickel: Preparation of Hexahydrobenzene
    • (c) Sabatier, P.; Senderens, J.-B. Direct Hydrogenation Realized in the Presence of Reduced Nickel: Preparation of Hexahydrobenzene. C. R. Hebd. Seances Acad. Sci. 1901, 132, 210.
    • (1901) C. R. Hebd. Seances Acad. Sci , vol.132 , pp. 210
    • Sabatier, P.1    Senderens, J.-B.2
  • 13
    • 0040196048 scopus 로고    scopus 로고
    • From Catalytic Hydrogenation to the Chemical Theory of the Catalysis: Paul Sabatier, Genius Chemist, Decentralization Apostle
    • For a biographical sketch of Paul Sabatier, see
    • For a biographical sketch of Paul Sabatier, see: Lattes, A. From Catalytic Hydrogenation to the Chemical Theory of the Catalysis: Paul Sabatier, Genius Chemist, Decentralization Apostle. C. R. Acad. Sci. Ser. IIC: Chem. 2000, 3, 705.
    • (2000) C. R. Acad. Sci. Ser. IIC: Chem , vol.3 , pp. 705
    • Lattes, A.1
  • 14
    • 37049159291 scopus 로고    scopus 로고
    • Prior to the work of Halpern and Wilkinson, the first transformations recognized as homogeneous hydrogenations involve the reduction of benzoquinone to the corresponding hydroquinone: (a) Calvin, M. Homogeneous Catalytic Hydrogenation. Trans. Faraday Soc. 1938, 34, 1181.
    • Prior to the work of Halpern and Wilkinson, the first transformations recognized as homogeneous hydrogenations involve the reduction of benzoquinone to the corresponding hydroquinone: (a) Calvin, M. Homogeneous Catalytic Hydrogenation. Trans. Faraday Soc. 1938, 34, 1181.
  • 15
    • 33947444407 scopus 로고
    • Homogeneous Catalytic Hydrogenation
    • (b) Calvin, M. Homogeneous Catalytic Hydrogenation. J. Am. Chem. Soc. 1939, 61, 2230.
    • (1939) J. Am. Chem. Soc , vol.61 , pp. 2230
    • Calvin, M.1
  • 16
    • 0000358159 scopus 로고    scopus 로고
    • Halpern, J.; Harrod, J. F.; James, B. R. Homogeneous Catalytic Hydrogenation of Olefinic Compounds. J. Am. Chem. Soc. 1961, 83, 753.
    • (a) Halpern, J.; Harrod, J. F.; James, B. R. Homogeneous Catalytic Hydrogenation of Olefinic Compounds. J. Am. Chem. Soc. 1961, 83, 753.
  • 17
    • 0001386191 scopus 로고
    • Homogeneous Catalysis of the Hydrogenation of Olefinic Compounds by Ruthenium(II)
    • (b) Halpern, J.; Harrod, J. F.; James, B. R. Homogeneous Catalysis of the Hydrogenation of Olefinic Compounds by Ruthenium(II) Chloride. J. Am. Chem. Soc. 1966, 88, 5150.
    • (1966) Chloride. J. Am. Chem. Soc , vol.88 , pp. 5150
    • Halpern, J.1    Harrod, J.F.2    James, B.R.3
  • 19
    • 3743070905 scopus 로고
    • Homogeneous Catalytic Hydrogenation and Hydroformylation of Acetylenic Compounds
    • (b) Jardine, F. H.; Osborn, J. A.; Wilkinson, G.; Young, J. F. Homogeneous Catalytic Hydrogenation and Hydroformylation of Acetylenic Compounds. Chem. Ind. 1965, 560.
    • (1965) Chem. Ind , pp. 560
    • Jardine, F.H.1    Osborn, J.A.2    Wilkinson, G.3    Young, J.F.4
  • 20
    • 37049054638 scopus 로고
    • Hydride Intermediates in Homogeneous Hydrogenation Reactions of Olefins and Acetylenes using Rhodium Catalysts
    • (c) Young, J. F.; Osborn, J. A.; Jardine, F. H.; Wilkinson, G. Hydride Intermediates in Homogeneous Hydrogenation Reactions of Olefins and Acetylenes using Rhodium Catalysts. Chem. Commun. 1965, 131.
    • (1965) Chem. Commun , pp. 131
    • Young, J.F.1    Osborn, J.A.2    Jardine, F.H.3    Wilkinson, G.4
  • 21
    • 33444462389 scopus 로고
    • Catalytic Asymmetric Hydrogenation Employing a Soluble Optically Active. Rhodium Complex
    • Knowles, W. S.; Sabacky, M. J. Catalytic Asymmetric Hydrogenation Employing a Soluble Optically Active. Rhodium Complex. Chem. Commun. 1968, 1445.
    • (1968) Chem. Commun , pp. 1445
    • Knowles, W.S.1    Sabacky, M.J.2
  • 22
    • 37049139019 scopus 로고
    • The Asymmetric Synthesis of Hydratropic Acid and Amino-Acids by Homogeneous Catalytic Hydrogenation
    • Dang, T. P.; Kagan, H. B. The Asymmetric Synthesis of Hydratropic Acid and Amino-Acids by Homogeneous Catalytic Hydrogenation. Chem. Commun. 1971, 481.
    • (1971) Chem. Commun , pp. 481
    • Dang, T.P.1    Kagan, H.B.2
  • 23
    • 1542694981 scopus 로고
    • Synthesis of 2,2′-bis(Diphenylphosphino)-1,1′-binaphthyl (BI-NAP), an Atropisomeric Chiral bis(Triaryl)phosphine, and its Use in the Rhodium(I)-Catalyzed Asymmetric Hydrogenation of α-(Acylamino)-acrylic Acids
    • Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. Synthesis of 2,2′-bis(Diphenylphosphino)-1,1′-binaphthyl (BI-NAP), an Atropisomeric Chiral bis(Triaryl)phosphine, and its Use in the Rhodium(I)-Catalyzed Asymmetric Hydrogenation of α-(Acylamino)-acrylic Acids. J. Am. Chem. Soc. 1980, 102, 7932.
    • (1980) J. Am. Chem. Soc , vol.102 , pp. 7932
    • Miyashita, A.1    Yasuda, A.2    Takaya, H.3    Toriumi, K.4    Ito, T.5    Souchi, T.6    Noyori, R.7
  • 28
    • 0000792656 scopus 로고
    • The Preparation of Synthetic Oil Mixtures (Synthol) from Carbon Monoxide and Hydrogen
    • (a) Fischer, F.; Tropsch, H. The Preparation of Synthetic Oil Mixtures (Synthol) from Carbon Monoxide and Hydrogen. Brennstoff Chem. 1923, 4, 276.
    • (1923) Brennstoff Chem , vol.4 , pp. 276
    • Fischer, F.1    Tropsch, H.2
  • 29
    • 0000789895 scopus 로고
    • Synthesis of Higher Members of the Aliphatic Series from Carbon Monoxide
    • (b) Fischer, F.; Tropsch, H. Synthesis of Higher Members of the Aliphatic Series from Carbon Monoxide. Chem. Ber. 1923, 56B, 2428.
    • (1923) Chem. Ber , vol.56 B , pp. 2428
    • Fischer, F.1    Tropsch, H.2
  • 32
    • 33745456767 scopus 로고    scopus 로고
    • Making Fuels Synthetically
    • Jacoby, M. Making Fuels Synthetically. Chem. Eng. News 2006, 84 (23), 57.
    • (2006) Chem. Eng. News , vol.84 , Issue.23 , pp. 57
    • Jacoby, M.1
  • 33
    • 0037812067 scopus 로고    scopus 로고
    • Chemische Verwertungsgesellschaft mbH, Oberhausen
    • German Patent DE 849, 548, 1938
    • Roelen, O. Chemische Verwertungsgesellschaft mbH, Oberhausen. German Patent DE 849, 548, 1938.
    • Roelen, O.1
  • 36
    • 0000193074 scopus 로고    scopus 로고
    • Prior to our work, two isolated examples of hydrogen-mediated C-C bond formations not involving carbon monoxide as a coupling partner were reported: (a) Molander, G. A.; Hoberg, J. O Organoyttrium-Catalyzed Cyclization of Substituted 1,5- and 1,6-Dienes. J. Am. Chem. Soc. 1992, 114, 3123.
    • Prior to our work, two isolated examples of hydrogen-mediated C-C bond formations not involving carbon monoxide as a coupling partner were reported: (a) Molander, G. A.; Hoberg, J. O Organoyttrium-Catalyzed Cyclization of Substituted 1,5- and 1,6-Dienes. J. Am. Chem. Soc. 1992, 114, 3123.
  • 37
    • 0001319755 scopus 로고
    • Rhodium-Catalyzed Reaction of Benzoic Anhydride with Styrene under Molecular Hydrogen
    • (b) Kokube, K.; Miura, M.; Nomura, M. Rhodium-Catalyzed Reaction of Benzoic Anhydride with Styrene under Molecular Hydrogen. Organometallics 1995, 14, 4521.
    • (1995) Organometallics , vol.14 , pp. 4521
    • Kokube, K.1    Miura, M.2    Nomura, M.3
  • 38
    • 33846995512 scopus 로고    scopus 로고
    • Side products of reductive C-C bond formation have been observed in catalytic hydrogenation on rare occasion: (a) Moyes, R. B, Walker, D. W, Wells, P. B, Whan, D. A, Irvine, E. A. Mechanism of Ethyne Hydrogenation in the Region of the Kinetic Discontinuity: Composition of C4 Products. Special Pub. Royal. Soc. Chem. 1992, 114, 207
    • Side products of reductive C-C bond formation have been observed in catalytic hydrogenation on rare occasion: (a) Moyes, R. B.; Walker, D. W.; Wells, P. B.; Whan, D. A.; Irvine, E. A. Mechanism of Ethyne Hydrogenation in the Region of the Kinetic Discontinuity: Composition of C4 Products. Special Pub. Royal. Soc. Chem. 1992, 114, 207.
  • 39
    • 0001450741 scopus 로고
    • Homogeneous Iron(II) System Capable of Selectivity Catalyzing the Reduction of Terminal Alkynes to Alkenes and Buta-1,3-dienes
    • (b) Bianchini, C.; Meli, A.; Peruzzini, M.; Vizzi, F.; Zanobini, F. Frediani, P. A Homogeneous Iron(II) System Capable of Selectivity Catalyzing the Reduction of Terminal Alkynes to Alkenes and Buta-1,3-dienes. Organometallics 1989, 8, 2080.
    • (1989) Organometallics , vol.8 , pp. 2080
    • Bianchini, C.1    Meli, A.2    Peruzzini, M.3    Vizzi, F.4    Zanobini, F.5    Frediani, P.A.6
  • 40
    • 0037176242 scopus 로고    scopus 로고
    • For rhodium-catalyzed reductive aldol reaction mediated by hydrogen, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. Use of Elemental Hydrogen for the Reductive Generation of Enolates from Enones: Catalytic C-C Bond Formation under Hydrogenative Conditions. J. Am. Chem. Soc. 2002, 124, 15156.
    • For rhodium-catalyzed reductive aldol reaction mediated by hydrogen, see: (a) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. Use of Elemental Hydrogen for the Reductive Generation of Enolates from Enones: Catalytic C-C Bond Formation under Hydrogenative Conditions. J. Am. Chem. Soc. 2002, 124, 15156.
  • 41
    • 32644453569 scopus 로고    scopus 로고
    • Hydrogen-Mediated Aldol Reductive Coupling of Vinyl Ketones Catalyzed by Rhodium: High Syn-Selectivity through the Effect of Tri-2-furylphosphine
    • (b) Jung, C.-K.; Garner, S. A.; Krische, M. J. 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, 519.
    • (2006) Org. Lett , vol.8 , pp. 519
    • Jung, C.-K.1    Garner, S.A.2    Krische, M.J.3
  • 42
    • 33845976661 scopus 로고    scopus 로고
    • Reductive Aldol Coupling of Divinyl Ketones via Rhodium Catalyzed Hydrogenation: Syn- Diastereoselective Construction of β-Hydroxyenones
    • (c) Han, S. B.; Krische, M. J. Reductive Aldol Coupling of Divinyl Ketones via Rhodium Catalyzed Hydrogenation: syn- Diastereoselective Construction of β-Hydroxyenones. Org. Lett. 2006, 8, 5657.
    • (2006) Org. Lett , vol.8 , pp. 5657
    • Han, S.B.1    Krische, M.J.2
  • 43
    • 33845917794 scopus 로고    scopus 로고
    • Asymmetric Induction in Hydrogen-Mediated Reductive Aldol Additions to α-Amino Aldehydes Catalyzed by Rhodium: Selective Formation of syn-Stereotriads Directed by Intramolecular Hydrogen-Bonding
    • (d) Jung, C. K.; Krische, M. J. Asymmetric Induction in Hydrogen-Mediated Reductive Aldol Additions to α-Amino Aldehydes Catalyzed by Rhodium: Selective Formation of syn-Stereotriads Directed by Intramolecular Hydrogen-Bonding. J. Am. Chem. Soc. 2006, 128, 17051.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 17051
    • Jung, C.K.1    Krische, M.J.2
  • 44
    • 0000191874 scopus 로고
    • 3
    • For rhodium-catalyzed reductive aldol reaction mediated by silane or other reductants, see: a
    • 3. Tetrahedron Lett. 1987, 28, 4809.
    • (1987) Tetrahedron Lett , vol.28 , pp. 4809
    • Revis, A.1    Hilty, T.K.2
  • 45
    • 0025062159 scopus 로고
    • Rhodium Catalyzed Direct Coupling of α,β-Unsaturated Ketone, Aldehyde, and Trialkylsilane: An Easy Access to Regio-Defined Aldol Derivatives
    • (b) Matsuda, I.; Takahashi, K.; Sata, S. Rhodium Catalyzed Direct Coupling of α,β-Unsaturated Ketone, Aldehyde, and Trialkylsilane: An Easy Access to Regio-Defined Aldol Derivatives. Tetrahedron Lett. 1990, 31, 5331.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5331
    • Matsuda, I.1    Takahashi, K.2    Sata, S.3
  • 46
    • 0033616095 scopus 로고    scopus 로고
    • Catalytic Diastereoselective Reductive Aldol Reaction: Optimization of Interdependent Reaction Variables by Arrayed Catalyst Evaluation
    • (c) Taylor, S. J.; Morken, J. P. Catalytic Diastereoselective Reductive Aldol Reaction: Optimization of Interdependent Reaction Variables by Arrayed Catalyst Evaluation. J. Am. Chem. Soc. 1999, 121, 12202.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 12202
    • Taylor, S.J.1    Morken, J.P.2
  • 47
    • 0034630894 scopus 로고    scopus 로고
    • Rhodium Catalyzed Enantioselective Reductive Aldol Reaction
    • (d) Taylor, S. J.; Duffey, M. O.; Morken, J. P. Rhodium Catalyzed Enantioselective Reductive Aldol Reaction. J. Am. Chem. Soc. 2000, 122, 4528.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 4528
    • Taylor, S.J.1    Duffey, M.O.2    Morken, J.P.3
  • 48
    • 0034904459 scopus 로고    scopus 로고
    • Some Preliminary Studies on a Novel Rhodium(I)-Catalysed Tandem Hydrosilylation-Intramolecular Aldol Reaction
    • (e) Emiabata-Smith, D.; McKillop, A.; Mills, C.; Motherwell, W. B.; Whitehead, A. J. Some Preliminary Studies on a Novel Rhodium(I)-Catalysed Tandem Hydrosilylation-Intramolecular Aldol Reaction. Synlett 2001, 1302.
    • (2001) Synlett , pp. 1302
    • Emiabata-Smith, D.1    McKillop, A.2    Mills, C.3    Motherwell, W.B.4    Whitehead, A.J.5
  • 49
    • 1342302796 scopus 로고    scopus 로고
    • Further Observations of the Rhodium(I) Catalysed Tandem Hydrosilylation- Intramolecular Aldol Reaction
    • (f) Freiría, M.; Whitehead, A. J.; Tocher, D. A.; Motherwell, W. B. Further Observations of the Rhodium(I) Catalysed Tandem Hydrosilylation- Intramolecular Aldol Reaction. Tetrahedron 2004, 60, 2673.
    • (2004) Tetrahedron , vol.60 , pp. 2673
    • Freiría, M.1    Whitehead, A.J.2    Tocher, D.A.3    Motherwell, W.B.4
  • 50
    • 20544434073 scopus 로고    scopus 로고
    • Direct Formation of Synthetically Useful Silyl-Protected Aldol Adducts via the Asymmetric Reductive Aldol Reaction
    • (g) Fuller, N. O.; Morken, J. P. Direct Formation of Synthetically Useful Silyl-Protected Aldol Adducts via the Asymmetric Reductive Aldol Reaction. Synlett 2005, 1459.
    • (2005) Synlett , pp. 1459
    • Fuller, N.O.1    Morken, J.P.2
  • 51
    • 18744395482 scopus 로고    scopus 로고
    • High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction: High Anti-Selectivity
    • (h) Nishiyama, H.; Siomi, T.; Tsuchiya, Y.; Matsuda, I. High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction: High Anti-Selectivity. J. Am. Chem. Soc. 2005, 127, 6972.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 6972
    • Nishiyama, H.1    Siomi, T.2    Tsuchiya, Y.3    Matsuda, I.4
  • 52
    • 29844444041 scopus 로고    scopus 로고
    • Rhodium-Catalyzed Reductive Aldol Reactions Using Aldehydes as Stoichiometric Reductants
    • (i) Willis, M. C.; Woodward, R. L. Rhodium-Catalyzed Reductive Aldol Reactions Using Aldehydes as Stoichiometric Reductants. J. Am. Chem. Soc. 2005, 127, 18012.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 18012
    • Willis, M.C.1    Woodward, R.L.2
  • 53
    • 33846962039 scopus 로고    scopus 로고
    • Cobalt(II) Catalyzed Coupling Reaction of α,β- Unsaturated Compounds with Aldehydes by the Use of Phenylsilane. New Method for the Preparation of β-Hydroxy Nitriles, Amides and Esters
    • For cobalt catalyzed reductive aldol reaction, see: a
    • For cobalt catalyzed reductive aldol reaction, see: (a) Isayama, S.; Mukaiyama, T. Cobalt(II) Catalyzed Coupling Reaction of α,β- Unsaturated Compounds with Aldehydes by the Use of Phenylsilane. New Method for the Preparation of β-Hydroxy Nitriles, Amides and Esters. Chem. Lett. 1989, 2005.
    • (2005) Chem. Lett , vol.1989
    • Isayama, S.1    Mukaiyama, T.2
  • 54
    • 0034803441 scopus 로고    scopus 로고
    • Diastereoselective Aldol and Michael Cycloreductions Catalyzed by Cobalt
    • (b) Baik, T.-G.; Luis, A. L.; Wang, L.-C.; Krische, M. J. Diastereoselective Aldol and Michael Cycloreductions Catalyzed by Cobalt. J. Am. Chem. Soc. 2001, 123, 5112.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 5112
    • Baik, T.-G.1    Luis, A.L.2    Wang, L.-C.3    Krische, M.J.4
  • 55
    • 0037077589 scopus 로고    scopus 로고
    • 2/Silane (dpm = 2,2.6.6-tetramethyl-heptane-3,5- dionate): Mechanism and Partitioning of Hydrometallative vs. Anion Radical Pathways. J. Am. Chem. Soc. 2002, 124, 9448.
    • 2/Silane (dpm = 2,2.6.6-tetramethyl-heptane-3,5- dionate): Mechanism and Partitioning of Hydrometallative vs. Anion Radical Pathways. J. Am. Chem. Soc. 2002, 124, 9448.
  • 56
    • 33748616837 scopus 로고    scopus 로고
    • Diastereoselective Cobalt-Catalyzed Reductive Aldol Cyclizations Using Diethylzinc as the Stoichiometric Reductant
    • (d) Lam, H. W.; Joensuu, P. M.; Murray, G. J.; Fordyce, E. A. F.; Prieto, O.; Luebbers, T. Diastereoselective Cobalt-Catalyzed Reductive Aldol Cyclizations Using Diethylzinc as the Stoichiometric Reductant. Org. Lett. 2006, 8, 3729.
    • (2006) Org. Lett , vol.8 , pp. 3729
    • Lam, H.W.1    Joensuu, P.M.2    Murray, G.J.3    Fordyce, E.A.F.4    Prieto, O.5    Luebbers, T.6
  • 57
    • 0001494417 scopus 로고    scopus 로고
    • For reductive aldol coupling catalyzed by other metals, see: Iridium: (a) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Enantio- and Diastereoselective Reductive Aldol Reactions with Iridium-Pybox Catalysts. Org. Lett. 2001, 3, 1829.
    • For reductive aldol coupling catalyzed by other metals, see: Iridium: (a) Zhao, C.-X.; Duffey, M. O.; Taylor, S. J.; Morken, J. P. Enantio- and Diastereoselective Reductive Aldol Reactions with Iridium-Pybox Catalysts. Org. Lett. 2001, 3, 1829.
  • 58
    • 0032537679 scopus 로고    scopus 로고
    • Palladium: (b) Kiyooka, S.; Shimizu, A.; Torii, S. A Mild Aldol Reaction of Aryl Aldehydes through Palladium-Catalyzed Hydrosilation of α,β-Unsaturated Carbonyl Compounds with Trichlorosilane. Tetrahedron Lett. 1998, 39, 5237.
    • Palladium: (b) Kiyooka, S.; Shimizu, A.; Torii, S. A Mild Aldol Reaction of Aryl Aldehydes through Palladium-Catalyzed Hydrosilation of α,β-Unsaturated Carbonyl Compounds with Trichlorosilane. Tetrahedron Lett. 1998, 39, 5237.
  • 60
    • 25444446131 scopus 로고    scopus 로고
    • Cu(I) Catalyzed Reductive Aldol Cyclizations: Diastereo- and Enantioselective Synthesis of β- Hydroxylactones
    • (d) Lam, H.-W.; Joensuu, P. M. Cu(I) Catalyzed Reductive Aldol Cyclizations: Diastereo- and Enantioselective Synthesis of β- Hydroxylactones. Org. Lett. 2005, 7, 4225.
    • (2005) Org. Lett , vol.7 , pp. 4225
    • Lam, H.-W.1    Joensuu, P.M.2
  • 61
    • 29444433067 scopus 로고    scopus 로고
    • Diastereoselective Synthesis of 4-Hydroxy-piperidin-2-ones via Cu(I)-Catalyzed Reductive Aldol Cyclization
    • (e) Lam, H.-W.; Murray, G. J.; Firth, J. D. Diastereoselective Synthesis of 4-Hydroxy-piperidin-2-ones via Cu(I)-Catalyzed Reductive Aldol Cyclization. Org. Lett. 2005, 7, 5743.
    • (2005) Org. Lett , vol.7 , pp. 5743
    • Lam, H.-W.1    Murray, G.J.2    Firth, J.D.3
  • 62
    • 31444451603 scopus 로고    scopus 로고
    • Catalytic Enantioselective Reductive Aldol Reaction to Ketones
    • (f) Zhao, D.; Oisaki, K.; Kanai, M.; Shibasaki, M. Catalytic Enantioselective Reductive Aldol Reaction to Ketones. Tetrahedron Lett. 2006, 47, 1403.
    • (2006) Tetrahedron Lett , vol.47 , pp. 1403
    • Zhao, D.1    Oisaki, K.2    Kanai, M.3    Shibasaki, M.4
  • 63
    • 33744913650 scopus 로고    scopus 로고
    • Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate
    • (g) Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Highly Diastereo- and Enantioselective Copper-Catalyzed Domino Reduction/Aldol Reaction of Ketones with Methyl Acrylate. Angew. Chem., Int. Ed. 2006, 45, 1292.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1292
    • Deschamp, J.1    Chuzel, O.2    Hannedouche, J.3    Riant, O.4
  • 64
    • 1042279655 scopus 로고    scopus 로고
    • Catalytic Generation of Indium Hydride in a Highly Diastereoselective Reductive Aldol Reaction
    • Indium: h
    • Indium: (h) Shibata, I.; Kato, H.; Ishida, T.; Yasuda, M.; Baba, A. Catalytic Generation of Indium Hydride in a Highly Diastereoselective Reductive Aldol Reaction. Angew. Chem., Int. Ed. 2004, 43, 711.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 711
    • Shibata, I.1    Kato, H.2    Ishida, T.3    Yasuda, M.4    Baba, A.5
  • 65
    • 4544247135 scopus 로고
    • Indium(III) Acetate-Catalyzed 1,4-Reduction and Reductive Aldol Reactions of α-Enones with Phenylsilane
    • (i) Miura, K.; Yamada, Y.; Tomita, M.; Hosomi, A. Indium(III) Acetate-Catalyzed 1,4-Reduction and Reductive Aldol Reactions of α-Enones with Phenylsilane. Synlett 2004, 1985.
    • (1985) Synlett , vol.2004
    • Miura, K.1    Yamada, Y.2    Tomita, M.3    Hosomi, A.4
  • 66
    • 0000131734 scopus 로고
    • Large Rate Accelerations in the Stille Reaction with Tri-2-furylphsophine and Triphenylarsine as Palladium Ligands: Mechanistic and Synthetic Implications
    • For tri-2-furylphosphine and triphenylarsine effects in metal-catalyzed reactions, see: a
    • For tri-2-furylphosphine and triphenylarsine effects in metal-catalyzed reactions, see: (a) Farina, V.; Krishnan, B. Large Rate Accelerations in the Stille Reaction with Tri-2-furylphsophine and Triphenylarsine as Palladium Ligands: Mechanistic and Synthetic Implications. J. Am. Chem. Soc. 1991, 113, 9585.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 9585
    • Farina, V.1    Krishnan, B.2
  • 67
    • 0002429680 scopus 로고    scopus 로고
    • New Perspectives in the Corss-Coupling Reactions of Organostannanes
    • (b) Farina, V. New Perspectives in the Corss-Coupling Reactions of Organostannanes. Pure Appl. Chem. 1996, 68, 73.
    • (1996) Pure Appl. Chem , vol.68 , pp. 73
    • Farina, V.1
  • 68
    • 0035323796 scopus 로고    scopus 로고
    • 2-Furylphosphines as Ligands for Transition-Metal-Mediated Organic Synthesis
    • (c) Anderson, N. G.; Keay, B. A. 2-Furylphosphines as Ligands for Transition-Metal-Mediated Organic Synthesis. Chem. Rev. 2001, 101, 997.
    • (2001) Chem. Rev , vol.101 , pp. 997
    • Anderson, N.G.1    Keay, B.A.2
  • 69
    • 33846972190 scopus 로고    scopus 로고
    • The anti-aldol diastereomers are thermodynamically preferred, Hence, high syn-diastereoselectivity suggests kinetic control at the stages of both enolization and aldol addition. For a review, see: Evans, D. A.; Nelson, J. V.; Taber, T. R. Stereoselective Aldol Condensations. Top. Stereochem. 1982, 13, 1.
    • The anti-aldol diastereomers are thermodynamically preferred, Hence, high syn-diastereoselectivity suggests kinetic control at the stages of both enolization and aldol addition. For a review, see: Evans, D. A.; Nelson, J. V.; Taber, T. R. Stereoselective Aldol Condensations. Top. Stereochem. 1982, 13, 1.
  • 70
    • 33847005800 scopus 로고    scopus 로고
    • Enones constrained in the s-trans configuration, such as cyclohexenone, do not participate in hydrogen-mediated reductive aldol coupling.
    • Enones constrained in the s-trans configuration, such as cyclohexenone, do not participate in hydrogen-mediated reductive aldol coupling.
  • 71
    • 33947468884 scopus 로고
    • Stereochemistry of the Ivanov and Reformatski Reaction
    • Zimmerman, H. E.; Traxler, M. D. Stereochemistry of the Ivanov and Reformatski Reaction. J. Am Chem. Soc. 1957, 79, 1920.
    • (1957) J. Am Chem. Soc , vol.79 , pp. 1920
    • Zimmerman, H.E.1    Traxler, M.D.2
  • 72
    • 33847804048 scopus 로고    scopus 로고
    • For mechanistic studies on alkene hydrogenation catalysed by neutral Rh(I) complexes, see: (a) Tolman, C. A.; Meakin, P. Z.; Lindner, D. L.; Jesson, J. P. Triarylphosphine, Hydride and Ethylene Complexes of Rhodium(I) Chloride. J. Am. Chem. Soc. 1974, 96, 2762.
    • For mechanistic studies on alkene hydrogenation catalysed by neutral Rh(I) complexes, see: (a) Tolman, C. A.; Meakin, P. Z.; Lindner, D. L.; Jesson, J. P. Triarylphosphine, Hydride and Ethylene Complexes of Rhodium(I) Chloride. J. Am. Chem. Soc. 1974, 96, 2762.
  • 73
    • 37049140380 scopus 로고
    • Hydrogenation of Tris(triphenylphosphine) chlororhodium-(I)
    • (b) Halpern, J.; Wong, C. S. Hydrogenation of Tris(triphenylphosphine) chlororhodium-(I). Chem. Commun. 1973, 629.
    • (1973) Chem. Commun , pp. 629
    • Halpern, J.1    Wong, C.S.2
  • 74
    • 49449122027 scopus 로고
    • Mechanism of the Chlorotris(triphenylphosphine) Rhodium(I) Catalyzed Hydrogenation of Alkenes. The Reaction of Chlorodihydidotris(triphenylphosphine)rhodium(III) with Cyclohexene
    • (c) Halpern, J.; Okamoto, T.; Zakhariev, A. Mechanism of the Chlorotris(triphenylphosphine) Rhodium(I) Catalyzed Hydrogenation of Alkenes. The Reaction of Chlorodihydidotris(triphenylphosphine)rhodium(III) with Cyclohexene. J. Mol. Catal. 1976, 2, 65.
    • (1976) J. Mol. Catal , vol.2 , pp. 65
    • Halpern, J.1    Okamoto, T.2    Zakhariev, A.3
  • 75
    • 33847797644 scopus 로고    scopus 로고
    • Monohydride catalytic cycles initiated via deprotonation of cationic rhodium dihydrides have been postulated: (a) Schrock, R. R, Osborn, J. A. Catalytic Hydrogenation Using Cationic Rhodium Complexes. I. Evolution of the Catalytic System and the Hydrogenation of Olefins. J. Am. Chem. Soc. 1976, 98, 2134
    • Monohydride catalytic cycles initiated via deprotonation of cationic rhodium dihydrides have been postulated: (a) Schrock, R. R.; Osborn, J. A. Catalytic Hydrogenation Using Cationic Rhodium Complexes. I. Evolution of the Catalytic System and the Hydrogenation of Olefins. J. Am. Chem. Soc. 1976, 98, 2134.
  • 76
    • 33845521170 scopus 로고
    • Catalytic Hydrogenation Using Cationic Rhodium Complexes. II. The Selective Hydrogenation of Alkynes to Cis Olefins
    • (b) Schrock, R. R.; Osborn, J. A. Catalytic Hydrogenation Using Cationic Rhodium Complexes. II. The Selective Hydrogenation of Alkynes to Cis Olefins. J. Am. Chem. Soc. 1976, 98, 2143.
    • (1976) J. Am. Chem. Soc , vol.98 , pp. 2143
    • Schrock, R.R.1    Osborn, J.A.2
  • 77
    • 0016972574 scopus 로고
    • Catalytic Hydrogenation Using Cationic Rhodium Complexes. 3. The Selective Hydrogenation of Dienes to Monoenes
    • (c) Schrock, R. R.; Osborn, J. A. Catalytic Hydrogenation Using Cationic Rhodium Complexes. 3. The Selective Hydrogenation of Dienes to Monoenes. J. Am. Chem. Soc. 1976, 98, 4450.
    • (1976) J. Am. Chem. Soc , vol.98 , pp. 4450
    • Schrock, R.R.1    Osborn, J.A.2
  • 78
    • 0002124260 scopus 로고
    • Acidity of Hydrido Transition Metal Complexes in Solution
    • For a review of the acidity of metal hydrides, see:, Dedieu, A, Ed, New York, Chapter 9
    • For a review of the acidity of metal hydrides, see: Norton, J. R. Acidity of Hydrido Transition Metal Complexes in Solution. In Transition Metal Hydrides; Dedieu, A., Ed.; New York, 1992; Chapter 9.
    • (1992) Transition Metal Hydrides
    • Norton, J.R.1
  • 79
    • 0034812506 scopus 로고    scopus 로고
    • Amino Acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond Formation
    • Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. Amino Acid Catalyzed Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic Asymmetric Carbon-Carbon Bond Formation. J. Am. Chem. Soc. 2001, 123, 5260.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 5260
    • Sakthivel, K.1    Notz, W.2    Bui, T.3    Barbas III, C.F.4
  • 80
    • 21244479264 scopus 로고    scopus 로고
    • Using amides of L-proline, direct catalyzed aldol coupling of 2-butanone to p-nitrobenzaldehyde affords mixtures of regioisomeric products: Tang, Z, Yang, Z.-H, Chen, X.-H, Cun, L.-F, Mi, A.-Q, Jiang, Y.-Z, Gong, L.-Z. A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldehydes. J. Am. Chem. Soc. 2005, 127, 9285
    • Using amides of L-proline, direct catalyzed aldol coupling of 2-butanone to p-nitrobenzaldehyde affords mixtures of regioisomeric products: Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. A Highly Efficient Organocatalyst for Direct Aldol Reactions of Ketones with Aldehydes. J. Am. Chem. Soc. 2005, 127, 9285.
  • 82
    • 0141534442 scopus 로고    scopus 로고
    • First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A New Regio-and Enantioselective C-C Bond Forming Hydrogenation
    • (a) Huddleston, R. R.; Jang, H.-Y.; Krische, M. J. "First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A New Regio-and Enantioselective C-C Bond Forming Hydrogenation," J. Am. Chem. Soc. 2003, 125, 11488.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 11488
    • Huddleston, R.R.1    Jang, H.-Y.2    Krische, M.J.3
  • 83
    • 0141649629 scopus 로고    scopus 로고
    • Catalytic C-C Bond Formation under Hydrogenation Conditions: Reductive Coupling of Dienes and Glyoxals
    • (b) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. "Catalytic C-C Bond Formation under Hydrogenation Conditions: Reductive Coupling of Dienes and Glyoxals," Angew. Chem., Int. Ed. 2003, 42, 4074.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 4074
    • Jang, H.-Y.1    Huddleston, R.R.2    Krische, M.J.3
  • 84
    • 1842788947 scopus 로고    scopus 로고
    • Hydrogen- Mediated C-C Bond Formation: Catalytic Regio- and Stereoselective Reductive Condensation of α-Ketoaldehydes and 1,3-Enynes
    • (c) Jang, H.-Y.; Huddleston, R. R.; Krische, M. J. "Hydrogen- Mediated C-C Bond Formation: Catalytic Regio- and Stereoselective Reductive Condensation of α-Ketoaldehydes and 1,3-Enynes," J. Am. Chem. Soc. 2004, 126, 4664.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 4664
    • Jang, H.-Y.1    Huddleston, R.R.2    Krische, M.J.3
  • 85
    • 0033913798 scopus 로고    scopus 로고
    • The catalytic reductive coupling of alkynes and carbonyl compounds has been achieved using nickel catalysts and stoichiometric reductants including diethylzinc, triethylborane and trialkylsilanes. For reviews encompassing this topic and related chemistry, see: (a) Montgomery, J. Nickel-Catalyzed Cyclizations, Couplings, and Cycloadditions Involving Three Reactive Components. Acc. Chem. Res. 2000, 33, 467
    • The catalytic reductive coupling of alkynes and carbonyl compounds has been achieved using nickel catalysts and stoichiometric reductants including diethylzinc, triethylborane and trialkylsilanes. For reviews encompassing this topic and related chemistry, see: (a) Montgomery, J. Nickel-Catalyzed Cyclizations, Couplings, and Cycloadditions Involving Three Reactive Components. Acc. Chem. Res. 2000, 33, 467.
  • 87
    • 0242467768 scopus 로고    scopus 로고
    • Nickel-Catalyzed Coupling of Carbonyl Compounds and Alkynes or 1,3-dienes: An Efficient Method for the Preparation of Allylic, Homoallylic, and Bishomoallylic Alcohols
    • (c) Ikeda, S.-I. Nickel-Catalyzed Coupling of Carbonyl Compounds and Alkynes or 1,3-dienes: An Efficient Method for the Preparation of Allylic, Homoallylic, and Bishomoallylic Alcohols. Angew. Chem., Int. Ed. 2003, 42, 5120.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 5120
    • Ikeda, S.-I.1
  • 88
    • 4544323639 scopus 로고    scopus 로고
    • Nickel-Catalyzed Reductive Cyclizations and Couplings
    • (d) Montgomery, J. Nickel-Catalyzed Reductive Cyclizations and Couplings. Angew. Chem., Int. Ed. 2004, 43, 3890.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 3890
    • Montgomery, J.1
  • 89
    • 33748625173 scopus 로고    scopus 로고
    • α-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes
    • (a) Cho, C.-W.; Krische, M. J. α-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes. Org. Lett. 2006, 8, 3873.
    • (2006) Org. Lett , vol.8 , pp. 3873
    • Cho, C.-W.1    Krische, M.J.2
  • 90
    • 33847002588 scopus 로고    scopus 로고
    • Catalytic Enantioselective Synthesis of Substituted Vinyl Glycines via Hydrogenative C-C Coupling of 1,3-Enynes and Ethyl Glyoxalate
    • Manuscript in preparation
    • (b) Hong, Y.-T.; Krische, M. J. Catalytic Enantioselective Synthesis of Substituted Vinyl Glycines via Hydrogenative C-C Coupling of 1,3-Enynes and Ethyl Glyoxalate, Manuscript in preparation.
    • Hong, Y.-T.1    Krische, M.J.2
  • 91
    • 31444453628 scopus 로고    scopus 로고
    • Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and α-Ketoesters via Rhodium Catalyzed Asymmetric Hydrogenation
    • Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and α-Ketoesters via Rhodium Catalyzed Asymmetric Hydrogenation. J. Am. Chem. Soc. 2006, 128, 718.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 718
    • Kong, J.-R.1    Ngai, M.-Y.2    Krische, M.J.3
  • 92
    • 33845961272 scopus 로고    scopus 로고
    • Enantioselective Reductive Coupling of 1,3-Enynes to Heterocyclic Aromatic Aldehydes and Ketones via Rhodium Catalyzed Asymmetric Hydrogenation
    • Komanduri, V.; Krische, M. J. Enantioselective Reductive Coupling of 1,3-Enynes to Heterocyclic Aromatic Aldehydes and Ketones via Rhodium Catalyzed Asymmetric Hydrogenation. J. Am. Chem. Soc. 2006, 128, 16448.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16448
    • Komanduri, V.1    Krische, M.J.2
  • 93
    • 23844494674 scopus 로고    scopus 로고
    • Hydrogen-Mediated Reductive Coupling of Conjugated Alkynes with Ethyl (N-sulfinyl)iminoacetates: Diastereoselective Synthesis of Unnatural α-Amino Acids via Rhodium Catalyzed C-C Bond Forming Hydrogenation
    • Kong, J.-R.; Cho, C.-W.; Krische, M. J. Hydrogen-Mediated Reductive Coupling of Conjugated Alkynes with Ethyl (N-sulfinyl)iminoacetates: Diastereoselective Synthesis of Unnatural α-Amino Acids via Rhodium Catalyzed C-C Bond Forming Hydrogenation. J. Am. Chem. Soc. 2005, 127, 11269.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 11269
    • Kong, J.-R.1    Cho, C.-W.2    Krische, M.J.3
  • 94
    • 2342570203 scopus 로고    scopus 로고
    • Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Brønsted Acid
    • (a) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchiba, K. Enantioselective Mannich-Type Reaction Catalyzed by a Chiral Brønsted Acid. Angew. Chem., Int. Ed. 2004, 116, 1566.
    • (2004) Angew. Chem., Int. Ed , vol.116 , pp. 1566
    • Akiyama, T.1    Itoh, J.2    Yokota, K.3    Fuchiba, K.4
  • 95
    • 2342521907 scopus 로고    scopus 로고
    • Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation
    • (b) Uraguchi, D.; Terada, M. Chiral Brønsted Acid-Catalyzed Direct Mannich Reactions via Electrophilic Activation. J. Am. Chem. Soc. 2004, 126, 5356.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 5356
    • Uraguchi, D.1    Terada, M.2
  • 96
    • 28044438742 scopus 로고    scopus 로고
    • Hoffman, S.; Seayad, A. M.; List, B. A Powerful Brønsted Acid Catalyst for the Organocatalytic Asymmetric Transfer Hydrogenation of Imines. Angew. Chem., Int. Ed. 2005, 117, 7424.
    • (c) Hoffman, S.; Seayad, A. M.; List, B. A Powerful Brønsted Acid Catalyst for the Organocatalytic Asymmetric Transfer Hydrogenation of Imines. Angew. Chem., Int. Ed. 2005, 117, 7424.
  • 97
    • 0037178064 scopus 로고    scopus 로고
    • Theoretical Study of Rhodium(III)-Catalyzed Hydrogenation of Carbon Dioxide into Formic Acid. Significant Differences in Reactivity among Rhodium(III), Rhodium(I), and Ruthenium-(II)
    • Musashi, Y.; Sakaki, S. Theoretical Study of Rhodium(III)-Catalyzed Hydrogenation of Carbon Dioxide into Formic Acid. Significant Differences in Reactivity among Rhodium(III), Rhodium(I), and Ruthenium-(II) Complexes. J. Am. Chem. Soc. 2002, 124, 7588.
    • (2002) Complexes. J. Am. Chem. Soc , vol.124 , pp. 7588
    • Musashi, Y.1    Sakaki, S.2
  • 98
    • 33747806634 scopus 로고    scopus 로고
    • Highly Enantioselective Reductive Cyclization of Acetylenic Aldehydes via Rhodium Catalyzed Asymmetric Hydrogenation
    • Rhee, J.-U.; Krische, M. J. Highly Enantioselective Reductive Cyclization of Acetylenic Aldehydes via Rhodium Catalyzed Asymmetric Hydrogenation. J. Am. Chem. Soc. 2006, 128, 10674.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 10674
    • Rhee, J.-U.1    Krische, M.J.2
  • 99
    • 33845585619 scopus 로고    scopus 로고
    • Catalytic Carbonyl (Z)-Dienylation via Multicomponent Reductive Coupling of Acetylene to Aldehydes and α-Ketoesters Mediated by Hydrogen: Carbonyl Insertion into Cationic Rhodocyclopentadienes
    • Kong, J.-R.; Krische, M. J. Catalytic Carbonyl (Z)-Dienylation via Multicomponent Reductive Coupling of Acetylene to Aldehydes and α-Ketoesters Mediated by Hydrogen: Carbonyl Insertion into Cationic Rhodocyclopentadienes. J. Am. Chem. Soc. 2006, 128, 16040.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16040
    • Kong, J.-R.1    Krische, M.J.2
  • 101
    • 33750488411 scopus 로고    scopus 로고
    • Branch-Selective Intermolecular Hydroacylation: Hydrogen-Mediated Coupling of Anhydrides to Styrenes and Activated Olefins
    • (a) Hong, Y.-T.; Barchuk, A.; Krische, M. J. Branch-Selective Intermolecular Hydroacylation: Hydrogen-Mediated Coupling of Anhydrides to Styrenes and Activated Olefins. Angew. Chem., Int. Ed. 2006, 128, 6885.
    • (2006) Angew. Chem., Int. Ed , vol.128 , pp. 6885
    • Hong, Y.-T.1    Barchuk, A.2    Krische, M.J.3
  • 102
    • 0001319755 scopus 로고
    • Rhodium-Catalyzed Reaction of Benzoic Anhydride with Styrene under Molecular Hydrogen
    • See also
    • (b) See also, Kokube, K.; Miura, M.; Nomura, M. Rhodium-Catalyzed Reaction of Benzoic Anhydride with Styrene under Molecular Hydrogen. Organometallics 1995, 14, 4521.
    • (1995) Organometallics , vol.14 , pp. 4521
    • Kokube, K.1    Miura, M.2    Nomura, M.3
  • 103
    • 49149142611 scopus 로고    scopus 로고
    • To suppress decarbonylation in intermolecular rhodium catalyzed hydroacylation, aldehyde donors that possess an adjacent site of coordination are required (for example, salicyladehydes and β-sulfidoaldehydes). Alternatively, conventional aldehyde donors may be converted to the corresponding (N-2-pyridyl)aldimines, which are then used as aldehyde equivalents: (a) Vora, K. P.; Lochow, C. F.; Miller, R. G. Rhodium Catalyzed Hydrogenation of Ethylene with 4-Pentenals. Reactions of 4-Hexenal-1-d. J. Organomet. Chem. 1980, 192, 257.
    • To suppress decarbonylation in intermolecular rhodium catalyzed hydroacylation, aldehyde donors that possess an adjacent site of coordination are required (for example, salicyladehydes and β-sulfidoaldehydes). Alternatively, conventional aldehyde donors may be converted to the corresponding (N-2-pyridyl)aldimines, which are then used as aldehyde equivalents: (a) Vora, K. P.; Lochow, C. F.; Miller, R. G. Rhodium Catalyzed Hydrogenation of Ethylene with 4-Pentenals. Reactions of 4-Hexenal-1-d. J. Organomet. Chem. 1980, 192, 257.
  • 104
    • 37049097448 scopus 로고
    • Rhodium Zeolites as Bifunctional Catalysts for the Synthesis of 2-Methylhexan-3-one and Heptan-4-one from Propylene. Carbon Monoxide, and Hydrogen
    • (b) Rode, E.; Davis, M. E.; Hanson, B. E. Rhodium Zeolites as Bifunctional Catalysts for the Synthesis of 2-Methylhexan-3-one and Heptan-4-one from Propylene. Carbon Monoxide, and Hydrogen. J. Chem. Soc., Chem. Commun. 1985, 716.
    • (1985) J. Chem. Soc., Chem. Commun , pp. 716
    • Rode, E.1    Davis, M.E.2    Hanson, B.E.3
  • 105
    • 33845278367 scopus 로고
    • Transition-Metal-Catalyzed C-C Bond Formation via C-H Activation. Intermolecular Hydroacylation: The Addition of Aldehydes to Alkenes
    • (c) Marder, T. B.; Roe, D. C.; Milstein, D. Transition-Metal-Catalyzed C-C Bond Formation via C-H Activation. Intermolecular Hydroacylation: The Addition of Aldehydes to Alkenes. Organometallics 1988, 7, 1451.
    • (1988) Organometallics , vol.7 , pp. 1451
    • Marder, T.B.1    Roe, D.C.2    Milstein, D.3
  • 106
    • 0000685510 scopus 로고    scopus 로고
    • Chelation-Assisted Intermolecular Hydroacylation: Direct Synthesis of Ketone from Aldehyde and 1-Alkene
    • (d) Jun, C.-H.; Lee, H.; Hong, J.-B. Chelation-Assisted Intermolecular Hydroacylation: Direct Synthesis of Ketone from Aldehyde and 1-Alkene. J. Org. Chem. 1997, 62, 1200.
    • (1997) J. Org. Chem , vol.62 , pp. 1200
    • Jun, C.-H.1    Lee, H.2    Hong, J.-B.3
  • 107
    • 0034283369 scopus 로고    scopus 로고
    • Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. A Highly Active Catalyst System for Intermolecular Hydroacylation. Angew. Chem., Int. Ed. 2000, 39, 3070.
    • (e) Jun, C.-H.; Lee, D.-Y.; Lee, H.; Hong, J.-B. A Highly Active Catalyst System for Intermolecular Hydroacylation. Angew. Chem., Int. Ed. 2000, 39, 3070.
  • 108
    • 0035898795 scopus 로고    scopus 로고
    • Solvent Free Chelation-Assisted Intermolecular Hydroacylation: Effect of Microwave Irradiation in the Synthesis of Ketone from Aldehyde and 1-Alkene by Rh(I) Complex
    • (f) Jun, C.-H.; Chung, J.-W.; Lee, D.-Y.; Loupy, A.; Chatti, S. Solvent Free Chelation-Assisted Intermolecular Hydroacylation: Effect of Microwave Irradiation in the Synthesis of Ketone from Aldehyde and 1-Alkene by Rh(I) Complex. Tetrahedron Lett. 2001, 42, 4803.
    • (2001) Tetrahedron Lett , vol.42 , pp. 4803
    • Jun, C.-H.1    Chung, J.-W.2    Lee, D.-Y.3    Loupy, A.4    Chatti, S.5
  • 109
    • 0035930763 scopus 로고    scopus 로고
    • Intermolecular Hydroacylation of Acrylate Esters: A New Route to 1,4-Diacrbonyls
    • (g) Willis, M. C.; Sapmaz, S. Intermolecular Hydroacylation of Acrylate Esters: A New Route to 1,4-Diacrbonyls. Chem. Commun. 2001, 2558.
    • (2001) Chem. Commun , pp. 2558
    • Willis, M.C.1    Sapmaz, S.2
  • 111
  • 112
    • 0346500648 scopus 로고    scopus 로고
    • Chelation-Controlled Intermolecular Hydroacylation: Direct Addition of Alkyl Aldehydes to Functionalized Alkenes
    • (j) Willis, M. C.; McNally, S. J.; Beswick, P. J. Chelation-Controlled Intermolecular Hydroacylation: Direct Addition of Alkyl Aldehydes to Functionalized Alkenes. Angew. Chem., Int. Ed. 2004, 43, 340.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 340
    • Willis, M.C.1    McNally, S.J.2    Beswick, P.J.3
  • 113
    • 23244446232 scopus 로고    scopus 로고
    • Rh-Catalyzed π-Facial Selective Intermolecular Hydroacylation of Norbornenes
    • (k) Tanaka, K.; Tanaka, M.; Suemune, H. Rh-Catalyzed π-Facial Selective Intermolecular Hydroacylation of Norbornenes. Tetrahedron Lett. 2005, 46, 6053.
    • (2005) Tetrahedron Lett , vol.46 , pp. 6053
    • Tanaka, K.1    Tanaka, M.2    Suemune, H.3
  • 114
    • 20444480207 scopus 로고    scopus 로고
    • Chelation-Controlled Intermolecular Alkene and Alkyne Hydroacylation: The Utility of β-Thioacetal Aldehydes
    • (l) Willis, M. C.; Randell-Sly, H. E.; Woodward, R. L.; Currie, G. S. Chelation-Controlled Intermolecular Alkene and Alkyne Hydroacylation: The Utility of β-Thioacetal Aldehydes. Org. Lett. 2005, 7, 2249.
    • (2005) Org. Lett , vol.7 , pp. 2249
    • Willis, M.C.1    Randell-Sly, H.E.2    Woodward, R.L.3    Currie, G.S.4
  • 115
    • 0001318808 scopus 로고
    • Oxidative Addition of Carboxylic Acid Anhydrides to Rhodium(I) Phosphine Complexes To Produce Novel Rhodium(III) Acyl Derivatives
    • Miller, J. A.; Nelson, J. A. Oxidative Addition of Carboxylic Acid Anhydrides to Rhodium(I) Phosphine Complexes To Produce Novel Rhodium(III) Acyl Derivatives. Organometallics 1991, 10, 2958.
    • (1991) Organometallics , vol.10 , pp. 2958
    • Miller, J.A.1    Nelson, J.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.