메뉴 건너뛰기




Volumn 32, Issue 7, 1999, Pages 605-613

Catalytic asymmetric addition reactions of carbonyls. A common catalytic approach

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; KETONE;

EID: 0032772355     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970347f     Document Type: Article
Times cited : (247)

References (46)
  • 7
    • 3242857105 scopus 로고
    • Chiral semicorrins and related nitrogen heterocycles as ligands in asymmetric catalysis
    • Pfaltz, A. Chiral Semicorrins and Related Nitrogen Heterocycles as Ligands in Asymmetric Catalysis. Acc. Chem. Res. 1993, 26, 339.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 339
    • Pfaltz, A.1
  • 10
    • 0342740235 scopus 로고
    • Bis(oxazoline)copper(II) complexes as chiral catalysts for the enantioselective Diels-Alder reaction
    • (b) Evans, D. A.; Miller, S. J.; Lectka, T. Bis(oxazoline)copper(II) Complexes as Chiral Catalysts for the Enantioselective Diels-Alder Reaction. J. Am. Chem. Soc. 1993, 115, 6469.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 6469
    • Evans, D.A.1    Miller, S.J.2    Lectka, T.3
  • 11
    • 33748726159 scopus 로고
    • 2-Symmetric cationic copper(II) complexes as Chiral Lewis acids: Counterion effects in the enantioselective Diels-Alder reaction
    • 2-Symmetric Cationic Copper(II) Complexes as Chiral Lewis Acids: Counterion Effects in the Enantioselective Diels-Alder Reaction. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 798
    • Evans, D.A.1    Murry, J.A.2    Matt, P.3    Norcross, R.D.4    Miller, S.J.5
  • 12
    • 0025042702 scopus 로고
    • Asymmetric catalytic cyclopropanation of olefins: Bis-oxazoline copper complexes
    • See, e.g.: (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Asymmetric Catalytic Cyclopropanation of Olefins: Bis-Oxazoline Copper Complexes. Tetrahedron Lett. 1990, 31, 6005.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 6005
    • Lowenthal, R.E.1    Abiko, A.2    Masamune, S.3
  • 13
    • 84987472013 scopus 로고
    • 2-symmetric 4,4′,5,5′-tetrahydrobi(oxazoles) and 4,4′,5,5′-tetrahydro-2,2′-methylenebis[oxazoles] as chiral ligands for enantioselective catalysis
    • 2-Symmetric 4,4′,5,5′-Tetrahydrobi(oxazoles) and 4,4′,5,5′-Tetrahydro-2,2′-methylenebis[oxazoles] as Chiral Ligands for Enantioselective Catalysis. Helv. Chim. Acta 1991, 74, 232.
    • (1991) Helv. Chim. Acta , vol.74 , pp. 232
    • Muller, D.1    Umbricht, G.2    Weber, B.3    Pfaltz, A.4
  • 14
    • 85008090337 scopus 로고
    • Bis(oxazolines) as chiral ligands in metal-catalyzed asymmetric reactions. Catalytic asymmetric cyclopropanation of olefins
    • Evans, D. A.; Woerpel, K. A.; Hinman, M. M.; Faul, M. M. Bis(oxazolines) as Chiral Ligands in Metal-Catalyzed Asymmetric Reactions. Catalytic Asymmetric Cyclopropanation of Olefins. J. Am. Chem. Soc. 1991, 113, 726.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 726
    • Evans, D.A.1    Woerpel, K.A.2    Hinman, M.M.3    Faul, M.M.4
  • 15
    • 33745424821 scopus 로고
    • Bis(oxazoline) als liganden für sich selbst organisierende, chirale koordinations polymere; struktur eines kupfer(I)-katalysators für die enantio selektive cyclopropanierung von olefinen
    • Evans, D. A.; Woerpel, K. A.; Scott, M. J. "Bis(oxazoline)" als Liganden für sich selbst organisierende, chirale Koordinations polymere; Struktur eines kupfer(I)-Katalysators für die enantio selektive Cyclopropanierung von Olefinen. Angew. Chem., Int. Ed. Engl. 1992, 32, 430.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.32 , pp. 430
    • Evans, D.A.1    Woerpel, K.A.2    Scott, M.J.3
  • 16
    • 0000303283 scopus 로고
    • Bis(oxazoline)-copper complexes as chiral catalysts for the enantioselective aziridination of olefins
    • (a) Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. Bis(oxazoline)-Copper Complexes as Chiral Catalysts for the Enantioselective Aziridination of Olefins. J. Am. Chem. Soc. 1993, 115, 5328.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5328
    • Evans, D.A.1    Faul, M.M.2    Bilodeau, M.T.3    Anderson, B.A.4    Barnes, D.M.5
  • 17
    • 33748236032 scopus 로고
    • Carbenoid transfer to imines: A new asymmetric catalytic synthesis of aziridines
    • (b) Hansen, K. B.; Finney, N. S.; Jacobsen, E. N. Carbenoid Transfer to Imines: A New Asymmetric Catalytic Synthesis of Aziridines. Angew. Chem., Int. Ed. Engl. 1995, 36, 676.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 676
    • Hansen, K.B.1    Finney, N.S.2    Jacobsen, E.N.3
  • 18
    • 84987263015 scopus 로고
    • Enantioselective allylic substitution catalyzed by chiral [bis (dihydrooxazole)] palladium complexes: Catalyst structure and possible mechanism of enantioselection
    • See, e.g.: van Matt, P.; Lloyd-Jones, G. C.; Minidis, A. B. E.; Pfaltz, A.; Macko, L.; Neuburger, M.; Zehnder, M.; Ruegger, H. Pregosin, P. S. Enantioselective Allylic Substitution Catalyzed by Chiral [Bis (dihydrooxazole)] palladium Complexes: Catalyst Structure and Possible Mechanism of Enantioselection. Helv. Chim. Acta 1995, 78, 265.
    • (1995) Helv. Chim. Acta , vol.78 , pp. 265
    • Van Matt, P.1    Lloyd-Jones, G.C.2    Minidis, A.B.E.3    Pfaltz, A.4    Macko, L.5    Neuburger, M.6    Zehnder, M.7    Ruegger, H.8    Pregosin, P.S.9
  • 19
    • 0028944316 scopus 로고
    • Enantioselective allylic oxidation catalyzed by chiral bisoxazoline-copper complexes
    • See, e.g.: Gokhale, A. S.; Minidis, A. B. E.; Pfaltz, A. Enantioselective Allylic Oxidation catalyzed by Chiral Bisoxazoline-Copper Complexes. Tetrahedron Lett. 1995, 36, 1831.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1831
    • Gokhale, A.S.1    Minidis, A.B.E.2    Pfaltz, A.3
  • 20
    • 0000822037 scopus 로고
    • Wu, j. H.; radinov, r.; porter, n. A. Enantioselective free radical carbon-carbon bond forming reactions: Chiral lewis acid promoted acyclic additions. J
    • See, e.g.: (a) Wu, J. H.; Radinov, R.; Porter, N. A. Enantioselective Free Radical Carbon-Carbon Bond Forming Reactions: Chiral Lewis Acid Promoted Acyclic Additions. J. Am. Chem. Soc. 1995, 117, 11029.
    • (1995) Am. Chem. Soc. , vol.117 , pp. 11029
  • 21
    • 0029804421 scopus 로고    scopus 로고
    • Chiral Lewis acid catalysis in radical reactions: Enantioselective conjugate radical additions
    • (b) Sibi, M. P. Ji, J.; Wu, J. H.; Gurtler, S.; Porter, N. A. Chiral Lewis Acid Catalysis in Radical Reactions: Enantioselective Conjugate Radical Additions. J. Am. Chem. Soc. 1996, 118, 9200.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9200
    • Sibi, M.P.1    Ji, J.2    Wu, J.H.3    Gurtler, S.4    Porter, N.A.5
  • 22
    • 0027319440 scopus 로고
    • Enantioselective conversion of aldehydes to cyanohydrins by a catalytic system with separate chiral binding sites for aldehyde and cyanide components
    • See, e.g.: Corey, E. J.; Wang, Z. Enantioselective Conversion of Aldehydes to Cyanohydrins by a Catalytic System with Separate Chiral Binding Sites for Aldehyde and Cyanide Components. Tetrahedron Lett. 1993, 34, 4001.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 4001
    • Corey, E.J.1    Wang, Z.2
  • 23
    • 0000034072 scopus 로고
    • Asymmetric addition of organolithium reagents to imines
    • See, e.g.: Denmark, S. E.; Nakajima, N.; Nicaise, O. J.-C. Asymmetric Addition of Organolithium Reagents to Imines. J. Am. Chem. Soc. 1994, 116, 8797.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 8797
    • Denmark, S.E.1    Nakajima, N.2    Nicaise, O.J.-C.3
  • 24
    • 0000157342 scopus 로고    scopus 로고
    • Control of diastereo-and enantioselectivity in metal-catalyzed 1,3-dipolar cycloaddition reactions of nitrones with alkenes. Experimental and theoretical investigations
    • See, e.g.: Gothelf, K. G.; Hazell, R. G.; Jørgensen, K. A. Control of Diastereo-and Enantioselectivity in Metal-Catalyzed 1,3-Dipolar Cycloaddition Reactions of Nitrones with Alkenes. Experimental and Theoretical Investigations. J. Org. Chem. 1996, 61, 346.
    • (1996) J. Org. Chem. , vol.61 , pp. 346
    • Gothelf, K.G.1    Hazell, R.G.2    Jørgensen, K.A.3
  • 25
    • 0000951665 scopus 로고
    • Asymmetric hetero Diels-Alder reactions and Ene reactions catalyzed by chiral copper(II) complexes. J. Org
    • (a) Johannsen, M.; Jørgensen, K. A. Asymmetric Hetero Diels-Alder Reactions and Ene Reactions Catalyzed by Chiral Copper(II) Complexes. J. Org. Chem. 1995, 60, 5757.
    • (1995) Chem. , vol.60 , pp. 5757
    • Johannsen, M.1    Jørgensen, K.A.2
  • 26
    • 0000600431 scopus 로고    scopus 로고
    • Metal-catalyzed hetero-Diels-Alder reactions of unactivated dienes with glyoxylates
    • (b) Johannsen, M.; Yao, S.; Graven, A.; Jørgensen, K. A. Metal-catalyzed Hetero-Diels-Alder Reactions of Unactivated dienes with Glyoxylates. Pure Appl. Chem. 1998, 79, 1117.
    • (1998) Pure Appl. Chem. , vol.79 , pp. 1117
    • Johannsen, M.1    Yao, S.2    Graven, A.3    Jørgensen, K.A.4
  • 27
    • 6744264109 scopus 로고
    • Asymmetric Ene reactions in organic synthesis
    • 2 have been developed: Mikami, K.; Shimizu, M. Asymmetric Ene Reactions in Organic Synthesis. Chem. Rev. 1992, 92, 1021.
    • (1992) Chem. Rev. , vol.92 , pp. 1021
    • Mikami, K.1    Shimizu, M.2
  • 28
    • 0029872590 scopus 로고    scopus 로고
    • Solvent effects in asymmetric hetero Diels-Alder and Ene reactions
    • (a) Johannsen, M.; Jørgensen, K. A. Solvent Effects in Asymmetric Hetero Diels-Alder and Ene Reactions. Tetrahedron 1996, 52, 7321.
    • (1996) Tetrahedron , vol.52 , pp. 7321
    • Johannsen, M.1    Jørgensen, K.A.2
  • 29
    • 0347768768 scopus 로고    scopus 로고
    • Solvent vs. Counterion acceleration of enantioselective carbo and Diels-Alder reactions
    • (b) Johannsen, M.; Jørgensen, K. A. Solvent vs. Counterion Acceleration of Enantioselective Carbo and Diels-Alder Reactions. J. Chem. Soc., Perkin Trans. 2 1997, 1183.
    • (1997) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1183
    • Johannsen, M.1    Jørgensen, K.A.2
  • 30
    • 0003084885 scopus 로고    scopus 로고
    • A highly chemo-and enantioselective Hetero-Diels-Alder reaction catalysed by chiral aluminium complexes
    • Graven, A.; Johannsen, M.; Jørgensen, K. A. A Highly Chemo-and Enantioselective Hetero-Diels-Alder Reaction Catalysed by Chiral Aluminium Complexes. J. Chem. Soc., Chem. Commun. 1996, 2373.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 2373
    • Graven, A.1    Johannsen, M.2    Jørgensen, K.A.3
  • 31
    • 0002428308 scopus 로고    scopus 로고
    • Total synthesis of (R)-dihydroactinidiolide and (R)-actinidiolide using asymmetric catalytic Hetero-Diels-Alder methodology
    • Yao, S.; Johannsen, M.; Hazell, R. G.; Jørgensen, K. A. Total Synthesis of (R)-Dihydroactinidiolide and (R)-Actinidiolide Using Asymmetric Catalytic Hetero-Diels-Alder Methodology. J. Org. Chem. 1998, 63, 118.
    • (1998) J. Org. Chem. , vol.63 , pp. 118
    • Yao, S.1    Johannsen, M.2    Hazell, R.G.3    Jørgensen, K.A.4
  • 32
    • 0032478649 scopus 로고    scopus 로고
    • Stereoselective synthesis of meso-2,6-diaminopimelic acid and its selectively protected derivatives
    • Gao, Y.; Lane-Bell, P.; Vederas, J. C. Stereoselective Synthesis of meso-2,6-Diaminopimelic Acid and Its Selectively Protected Derivatives. J. Org. Chem. 1998, 63, 2133.
    • (1998) J. Org. Chem. , vol.63 , pp. 2133
    • Gao, Y.1    Lane-Bell, P.2    Vederas, J.C.3
  • 33
    • 0032540647 scopus 로고    scopus 로고
    • 2-symmetric copper(II) complexes as chiral Lewis acids. Enantioselective catalysis of the Glyoxylate-Ene reaction
    • 2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Enantioselective Catalysis of the Glyoxylate-Ene Reaction. J. Am. Chem. Soc. 1998, 120, 5824.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5824
    • Evans, D.A.1    Burgey, C.S.2    Paras, N.A.3    Vojlovsky, T.4    Tregay, S.W.5
  • 34
    • 0002816322 scopus 로고    scopus 로고
    • The first highly enantioselective catalytic hetero Diels-Alder reaction of ketones
    • (a) Johannsen, M.; Yao, S.; Jørgensen, K. A. The First Highly Enantioselective Catalytic Hetero Diels-Alder Reaction of Ketones. J. Chem. Soc., Chem. Commun. 1997, 2169.
    • (1997) J. Chem. Soc., Chem. Commun. , pp. 2169
    • Johannsen, M.1    Yao, S.2    Jørgensen, K.A.3
  • 35
    • 0032475445 scopus 로고    scopus 로고
    • Catalytic asymmetric Hetero-Diels-Alder reactions of ketones: Chemzymatic reactions
    • (b) Yao, S.; Johannsen, M.; Audrain, H.; Hazell, R. G.; Jørgensen, K. A. Catalytic Asymmetric Hetero-Diels-Alder Reactions of Ketones: Chemzymatic Reactions. J. Am. Chem. Soc. 1998, 120, 8599.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 8599
    • Yao, S.1    Johannsen, M.2    Audrain, H.3    Hazell, R.G.4    Jørgensen, K.A.5
  • 36
    • 0032473509 scopus 로고    scopus 로고
    • The catalytic enantioselective construction of molecules with quaternary carbon stereocenters
    • Corey, E. J.; Guzman-Perez, A. The Catalytic Enantioselective Construction of Molecules with Quaternary Carbon Stereocenters. Angew. Chem., Int. Ed. Engl. 1998, 37, 388.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 388
    • Corey, E.J.1    Guzman-Perez, A.2
  • 38
    • 0001443088 scopus 로고    scopus 로고
    • Catalytic enantioselective hetero Diels-Alder reactions of α,β-unsaturated acyl phosphonates with enol ethers
    • Evans, D. A.; Johnson, J. S. Catalytic Enantioselective Hetero Diels-Alder Reactions of α,β-Unsaturated Acyl Phosphonates with Enol Ethers. J. Am. Chem. Soc. 1998, 120, 4895.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4895
    • Evans, D.A.1    Johnson, J.S.2
  • 39
    • 0032544310 scopus 로고    scopus 로고
    • Highly enantioselective catalytic Hetero-Diels-Alder reaction with inverse electron demand
    • Thorhauge, J.; Johannsen, M.; Jørgensen, K. A. Highly Enantioselective Catalytic Hetero-Diels-Alder Reaction with Inverse Electron Demand. Angew. Chem., Int. Ed. Engl. 1998, 37, 2404.
    • (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 2404
    • Thorhauge, J.1    Johannsen, M.2    Jørgensen, K.A.3
  • 40
    • 0032512595 scopus 로고    scopus 로고
    • Catalyzed enantioselective aldol additions of latent enolate equivalents
    • See, e.g.: (a) Nelson, S. G. Catalyzed Enantioselective Aldol Additions of Latent Enolate Equivalents. Tetrahedron: Asymmetry 1998, 9, 357.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 357
    • Nelson, S.G.1
  • 41
    • 0030952586 scopus 로고    scopus 로고
    • 2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
    • 2-Symmetric Copper(II) Complexes as Chiral Lewis Acids. Catalytic Enantioselective Aldol Additions of Enolsilanes to Pyruvate Esters. J. Am. Chem. Soc. 1997, 119, 7893.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7893
    • Evans, D.A.1    Kozlowski, M.C.2    Burgey, C.S.3    Macmillan, D.W.C.4
  • 42
    • 0030781007 scopus 로고    scopus 로고
    • 2-symmetric tin(II) complexes as chiral lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
    • 2-Symmetric Tin(II) Complexes as Chiral Lewis Acids. Catalytic Enantioselective Anti Aldol Additions of Enolsilanes to Glyoxylate and Pyruvate Esters. J. Am. Chem. Soc. 1997, 119, 10859.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10859
    • Evans, D.A.1    Macmillan, D.W.C.2    Campos, K.R.3
  • 43
    • 0000070865 scopus 로고    scopus 로고
    • An improved procedure for the preparation of 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane[(S,S)-tert-Butyl- bis(oxazoline)] and derived copper(II) complexes
    • Evans, D. A.; Peterson, G. S.; Johnson, J. J.; Barnes, D. M.; Canpos, K. R.; Woerpel, K. A. An Improved Procedure for the Preparation of 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane[(S,S)-tert-Butyl- bis(oxazoline)] and Derived Copper(II) Complexes. J. Org. Chem. 1998, 63, 4541.
    • (1998) J. Org. Chem. , vol.63 , pp. 4541
    • Evans, D.A.1    Peterson, G.S.2    Johnson, J.J.3    Barnes, D.M.4    Canpos, K.R.5    Woerpel, K.A.6
  • 45
    • 0030583498 scopus 로고    scopus 로고
    • Cationic Bis(oxazoline) and Pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis acid catalysts. A comparative study in catalysis of Diels-Alder and aldol reactions
    • Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Cationic Bis(oxazoline) and Pyridyl-bis(oxazoline)Cu(II) and Zn(II) Lewis Acid Catalysts. A Comparative Study in Catalysis of Diels-Alder and Aldol Reactions. Tetrahedron Lett. 1996, 37, 7481.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7481
    • Evans, D.A.1    Kozlowski, M.C.2    Tedrow, J.S.3
  • 46
    • 0029881335 scopus 로고    scopus 로고
    • The first enantio selective synthesis of both Diels-Alder enantiomers with the same bis(oxazoline)-magnesium perchlorate catalyst
    • See also: Desmoni, G.; Faita, G.; Righetti, P. P. The First Enantio selective Synthesis of Both Diels-Alder Enantiomers with the Same bis(oxazoline)-Magnesium Perchlorate Catalyst. Tetrahedron Lett. 1996, 37, 3027.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3027
    • Desmoni, G.1    Faita, G.2    Righetti, P.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.