메뉴 건너뛰기




Volumn 33, Issue 6, 2000, Pages 346-353

Phosphoramidites: Marvellous ligands in catalytic asymmetric conjugate addition

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; COPPER; CYCLOALKANONE; HYDROCARBON; KETONE; LIGAND; ORGANOLITHIUM COMPOUND; ORGANOMETALLIC COMPOUND; ORGANOPHOSPHORUS COMPOUND; PHOSPHORAMIDIC ACID DERIVATIVE; PHOSPHORAMIDITE DERIVATIVE; STEROID; UNCLASSIFIED DRUG; ZINC; ZINC DERIVATIVE;

EID: 0033935279     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar990084k     Document Type: Article
Times cited : (700)

References (69)
  • 7
    • 0003280270 scopus 로고
    • Conjugate addition reactions in organic synthesis
    • Pergamon: Oxford
    • Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series 9; Pergamon: Oxford, 1992.
    • (1992) Tetrahedron Organic Chemistry Series , vol.9
    • Perlmutter, P.1
  • 8
    • 0030788440 scopus 로고    scopus 로고
    • Asymmetric catalysis with heterobimetallic compounds
    • Shibasaki, M.; Sasai, H.; Arai, T. Asymmetric catalysis with heterobimetallic compounds. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1236-1256
    • Shibasaki, M.1    Sasai, H.2    Arai, T.3
  • 9
    • 33845374924 scopus 로고
    • Enantioselective conjugate addition of rationally designed chiral cuprate reagents to 2-cycloalkenones
    • Corey, E. J.; Naef, R.; Hannon, F. Enantioselective conjugate addition of rationally designed chiral cuprate reagents to 2-cycloalkenones. J. Am. Chem. Soc. 1986, 108, 7114-7116.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7114-7116
    • Corey, E.J.1    Naef, R.2    Hannon, F.3
  • 10
    • 0001040147 scopus 로고
    • Asymmetric conjugate addition
    • (a) Rossiter, B. E.; Swingle, N. M. Asymmetric conjugate addition. Chem. Rev. 1992, 92, 771-806.
    • (1992) Chem. Rev. , vol.92 , pp. 771-806
    • Rossiter, B.E.1    Swingle, N.M.2
  • 11
    • 0001068768 scopus 로고
    • Carbon-carbon bond formation by catalytic enantioselective conjugate addition
    • Asymmetric chemical transformations; Doyle, M. D., Ed.; JAI Press Inc.: Greenwich, CT
    • (b) Feringa, B. L.; de Vries, A. H. M. Carbon-Carbon bond formation by Catalytic Enantioselective Conjugate Addition. In Asymmetric chemical transformations; Doyle, M. D., Ed.; Advances in Catalytic Processes 1; JAI Press Inc.: Greenwich, CT, 1995; pp 151-192.
    • (1995) Advances in Catalytic Processes , vol.1 , pp. 151-192
    • Feringa, B.L.1    De Vries, A.H.M.2
  • 12
    • 0032536551 scopus 로고    scopus 로고
    • Copper-catalyzed enantioselective Michael additions: Recent progress with new phosphorus ligands
    • (c) Krause, N. Copper-catalyzed enantioselective Michael additions: Recent progress with new phosphorus ligands. Angew. Chem., Int. Ed. 1998, 37, 283-285.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 283-285
    • Krause, N.1
  • 13
    • 0001620795 scopus 로고
    • Synthesis and reactivity of binuclear tropocoronol and related organocopper(I) complexes. Catalytic enantioselective conjugate addition of grignard reagents to 2-cyclohexen-1-one
    • Villacorta, G. M.; Rao, C. P.; Lippard, S. J. Synthesis and reactivity of binuclear tropocoronol and related organocopper(I) complexes. Catalytic enantioselective conjugate addition of Grignard reagents to 2-cyclohexen-1-one. J. Am. Chem. Soc. 1988, 110, 3175-3182.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3175-3182
    • Villacorta, G.M.1    Rao, C.P.2    Lippard, S.J.3
  • 14
    • 0001407478 scopus 로고
    • A new class of organocopper and organocuprate compounds derived from copper(I) arenethiolates
    • (a) Knotter, D. M.; Grove, D. M.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. A new class of organocopper and organocuprate compounds derived from copper(I) arenethiolates, J. Am. Chem. Soc. 1992, 114, 3400-3410.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3400-3410
    • Knotter, D.M.1    Grove, D.M.2    Smeets, W.J.J.3    Spek, A.L.4    Van Koten, G.5
  • 15
    • 0027501888 scopus 로고
    • Chiral mercapto aryl-oxazolines as ligands in asymmetric catalysis: Enantioselective Cu-catalyzed 1,4-addition of grignard reagents to α,β-unsaturated ketones
    • (b) Zhou, Q.-L.; Pfaltz, A. Chiral mercapto aryl-oxazolines as ligands in asymmetric catalysis: Enantioselective Cu-catalyzed 1,4-addition of Grignard reagents to α,β-unsaturated ketones. Tetrahedron Lett. 1993, 34, 7725-7728.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7725-7728
    • Zhou, Q.-L.1    Pfaltz, A.2
  • 16
    • 84987539004 scopus 로고
    • Enantioselective copper-catalyzed 1,4-addition of grignard reagents to α,β-unsaturated carbonyl compounds
    • (c) Spescha, M.; Rihs, G. Enantioselective copper-catalyzed 1,4-addition of Grignard reagents to α,β-unsaturated carbonyl compounds. Helv. Chim. Acta 1993, 76, 1219-1230.
    • (1993) Helv. Chim. Acta , vol.76 , pp. 1219-1230
    • Spescha, M.1    Rihs, G.2
  • 17
    • 0000386896 scopus 로고    scopus 로고
    • Enantioselective 1,4-addition of aliphatic Grignard reagents to enones catalyzed by readily available copper(I) thiolates derived from TADDOL
    • (d) Seebach, D.; Jeasche, G.; Pichota, A.; Audergon, L. Enantioselective 1,4-addition of aliphatic Grignard reagents to enones catalyzed by readily available copper(I) thiolates derived from TADDOL. Helv. Chim. Acta 1997, 80, 2515-2519.
    • (1997) Helv. Chim. Acta , vol.80 , pp. 2515-2519
    • Seebach, D.1    Jeasche, G.2    Pichota, A.3    Audergon, L.4
  • 18
    • 0029044287 scopus 로고
    • Catalytic asymmetric conjugate addition of Grignard reagents mediated by copper(I) chiral bidentate phosphine complex
    • (e) Kanai, M.; Tomioka, K. Catalytic asymmetric conjugate addition of Grignard reagents mediated by copper(I) chiral bidentate phosphine complex. Tetrahedron Lett. 1995, 36, 4275-4278.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4275-4278
    • Kanai, M.1    Tomioka, K.2
  • 19
    • 37049084174 scopus 로고
    • Zinc(II)-catalysed conjugate addition of Grignard reagents to α,β-unsaturated ketones
    • (f) Jansen, J. F. G. A.; Feringa, B. L. Zinc(II)-catalysed conjugate addition of Grignard reagents to α,β-unsaturated ketones. J. Chem. Soc., Chem. Commun. 1989, 741-742.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 741-742
    • Jansen, J.F.G.A.1    Feringa, B.L.2
  • 20
    • 0000032365 scopus 로고
    • Enantioselective conjugate addition of Grignard reagents to enones catalysed by chiral zinc(II)-complexes
    • (g) Jansen, J. F. G. A.; Feringa, B. L. Enantioselective conjugate addition of Grignard reagents to enones catalysed by chiral zinc(II)-complexes. J. Org. Chem. 1990, 55, 4168-4175.
    • (1990) J. Org. Chem. , vol.55 , pp. 4168-4175
    • Jansen, J.F.G.A.1    Feringa, B.L.2
  • 21
    • 37049074156 scopus 로고
    • Chiral amplification and the catalytic process in the enantioselective conjugate addition of chiral alkoxy-dimethylcuprate to (E)-cyclopentadec-2-en-1-one
    • (h) A notable exception is the chiral alkoxycuprate-catalyzed addition of MeLi to afford (R)-muscone with an impressive 99% ee, reported by Tanaka et al.: Tanaka, K.; Matsui, J.; Suzuki, H. Chiral amplification and the catalytic process in the enantioselective conjugate addition of chiral alkoxy-dimethylcuprate to (E)-cyclopentadec-2-en-1-one. J. Chem. Soc., Perkin Trans. 1 1993, 153-157.
    • (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 153-157
    • Tanaka, K.1    Matsui, J.2    Suzuki, H.3
  • 22
    • 0001158063 scopus 로고    scopus 로고
    • Alkylation of carbonyl groups
    • Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Chapter 26.1
    • For a recent review, see: Soai, K.; Shibata, T. Alkylation of Carbonyl Groups. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vols. I-III, Chapter 26.1.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1-3
    • Soai, K.1    Shibata, T.2
  • 23
    • 0031573812 scopus 로고    scopus 로고
    • Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents
    • Feringa, B. L.; Pineschi, M.; Arnold, L. A.; Imbos, R.; de Vries, A. H. M. Highly enantioselective catalytic conjugate addition and tandem conjugate addition - aldol reactions of organozinc reagents. Angew. Chem., Int. Ed. Engl. 1997, 36, 2620-2623.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2620-2623
    • Feringa, B.L.1    Pineschi, M.2    Arnold, L.A.3    Imbos, R.4    De Vries, A.H.M.5
  • 24
    • 4243489506 scopus 로고
    • Preparation and reactions of polyfunctional organozinc reagents in organic synthesis
    • (a) Knochel, P.; Singer, R. D. Preparation and reactions of polyfunctional organozinc reagents in organic synthesis. Chem. Rev. 1993, 93, 2117-2188.
    • (1993) Chem. Rev. , vol.93 , pp. 2117-2188
    • Knochel, P.1    Singer, R.D.2
  • 25
    • 0001454803 scopus 로고    scopus 로고
    • Downsizing copper in modern cuprate couplings
    • (b) Lipschutz, B. H. Downsizing Copper in Modern Cuprate Couplings. Acc. Chem. Res. 1997, 30, 277-282.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 277-282
    • Lipschutz, B.H.1
  • 26
    • 84918678077 scopus 로고
    • Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides
    • (a) Kumada, M. Nickel and palladium complex catalyzed cross-coupling reactions of organometallic reagents with organic halides. Pure Appl. Chem. 1980, 52, 669-679.
    • (1980) Pure Appl. Chem. , vol.52 , pp. 669-679
    • Kumada, M.1
  • 27
    • 0001419934 scopus 로고
    • Efficient synthesis of (±)-β-cuparenone. Conjugate addition of organozinc reactions
    • (b) Greene, A. E.; Lansard, J. P.; Luche, J. L.; Petrier, C. Efficient synthesis of (±)-β-cuparenone. Conjugate addition of organozinc reactions. J. Org. Chem. 1984, 49, 931-932.
    • (1984) J. Org. Chem. , vol.49 , pp. 931-932
    • Greene, A.E.1    Lansard, J.P.2    Luche, J.L.3    Petrier, C.4
  • 28
    • 33845280673 scopus 로고
    • Synthesis and reactivity toward acylchlorides and enones of the new highly functionalised copper reagents RCu(CN)Znl
    • (a) Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. Synthesis and reactivity toward acylchlorides and enones of the new highly functionalised copper reagents RCu(CN)Znl. J. Org. Chem. 1988, 53, 2390-2392.
    • (1988) J. Org. Chem. , vol.53 , pp. 2390-2392
    • Knochel, P.1    Yeh, M.C.P.2    Berk, S.C.3    Talbert, J.4
  • 29
    • 84990134835 scopus 로고
    • Copper (I)-promoted Michael-addition reactions of organozincs of esters, nitriles and α-aminoacids
    • (b) Tamaru, Y.; Tanigawa, H.; Yamamoto, T.; Yoshida, Z. Copper (I)-promoted Michael-addition reactions of organozincs of esters, nitriles and α-aminoacids. Angew. Chem., Int. Ed. Engl. 1989, 28, 351-353.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 351-353
    • Tamaru, Y.1    Tanigawa, H.2    Yamamoto, T.3    Yoshida, Z.4
  • 30
    • 0000358709 scopus 로고
    • The direct formation of functionalised alkyl (aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, α,β-unsaturated ketones and allylic, aryl and vinyl halides
    • (c) Zhu, L.; Wehmeyer, R. M.; Rieke, R. D. The direct formation of functionalised alkyl (aryl)zinc halides by oxidative addition of highly reactive zinc with organic halides and their reactions with acid chlorides, α,β-unsaturated ketones and allylic, aryl and vinyl halides. J. Org. Chem. 1991, 56, 1445-1453.
    • (1991) J. Org. Chem. , vol.56 , pp. 1445-1453
    • Zhu, L.1    Wehmeyer, R.M.2    Rieke, R.D.3
  • 31
    • 0000591250 scopus 로고
    • Michael additions of functionalised organozinc reagents mediated by catalytic quantities of copper(I)
    • (d) Lipschutz, B. H.; Wood, M. R.; Tirado, R. Michael additions of functionalised organozinc reagents mediated by catalytic quantities of copper(I). J. Am. Chem. Soc. 1995, 117, 6126-6127.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6126-6127
    • Lipschutz, B.H.1    Wood, M.R.2    Tirado, R.3
  • 32
    • 33750026643 scopus 로고
    • Palladium- or nickel-catalysed cross-coupling. A new selective method for C-C bond formation
    • Negishi, E. Palladium- or nickel-catalysed cross-coupling. A new selective method for C-C bond formation. Acc. Chem. Res. 1982, 15, 340-348.
    • (1982) Acc. Chem. Res. , vol.15 , pp. 340-348
    • Negishi, E.1
  • 33
    • 33748234330 scopus 로고
    • Titanate-catalysed enantioselective addition of dialkylzinc compounds-generated in situ from grignard in ether - To aldehydes
    • (a) Seebach, D.; Behrendt, L.; Felix, D. Titanate-catalysed enantioselective addition of dialkylzinc compounds-generated in situ from Grignard in ether - to aldehydes. Angew. Chem., Int. Ed. Engl. 1991, 30, 1008-1009.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1008-1009
    • Seebach, D.1    Behrendt, L.2    Felix, D.3
  • 34
    • 0001323711 scopus 로고
    • Chiral titanium complexes for enantioselective addition of nucleophiles to carbonyl groups
    • (b) Duthaler, R. O.; Hafner, A. Chiral Titanium complexes for enantioselective addition of nucleophiles to carbonyl groups. Chem. Rev. 1992, 92, 807.
    • (1992) Chem. Rev. , vol.92 , pp. 807
    • Duthaler, R.O.1    Hafner, A.2
  • 35
    • 0027263635 scopus 로고
    • Enantioselective preparation of polyfunctional secondary allylic alcohols using polyfunctionalised dialkylzincs prepared by a copper(I)-catalysed iodine-zinc exchange
    • (c) Rozema, M. J.; Eisenberg, C.; Lutjens, H.; Ostwald, R.; Belyk, K.; Knochel, P. Enantioselective preparation of polyfunctional secondary allylic alcohols using polyfunctionalised dialkylzincs prepared by a copper(I)-catalysed Iodine-zinc exchange. Tetrahedron Lett. 1993, 34, 3115-3118.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3115-3118
    • Rozema, M.J.1    Eisenberg, C.2    Lutjens, H.3    Ostwald, R.4    Belyk, K.5    Knochel, P.6
  • 36
    • 0001784175 scopus 로고
    • Catalytic enantioselective conjugate addition of dialkylzincs to α,β-unsaturated ketones using nickelbromide-N,N-dibutylnorephedrine
    • (a) Soai, K.; Hayasaka, T.; Ugajin, S. J.; Yokoyoma, S. Catalytic enantioselective conjugate addition of dialkylzincs to α,β-unsaturated ketones using nickelbromide-N,N-dibutylnorephedrine. Chem. Lett. 1988, 1571-1572.
    • (1988) Chem. Lett. , pp. 1571-1572
    • Soai, K.1    Hayasaka, T.2    Ugajin, S.J.3    Yokoyoma, S.4
  • 37
    • 0025182122 scopus 로고
    • Optically active bipyridines in nickel catalysed enantioselective conjugate additions to enones
    • (b) Bolm, C.; Ewald, M. Optically active bipyridines in nickel catalysed enantioselective conjugate additions to enones. Tetrahedron Lett. 1990, 31, 5011-5012.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 5011-5012
    • Bolm, C.1    Ewald, M.2
  • 38
    • 0026666877 scopus 로고
    • Catalytic enantioselective conjugate additions of diethylzinc using Ni(II)DAIB-complexes
    • (c) Jansen, J. F. G. A.; Feringa, B. L. Catalytic enantioselective conjugate additions of diethylzinc using Ni(II)DAIB-complexes. Tetrahedron: Asymmetry 1992, 3, 581-582.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 581-582
    • Jansen, J.F.G.A.1    Feringa, B.L.2
  • 39
    • 0026710601 scopus 로고
    • Enantioselective conjugate addition of diethylzinc to chalcone catalyzed by chiral tricarbonyl-(arene)chromium/nickel(II)
    • (d) Uemura, M.; Miyaki, R.; Nakayama, K.; Hayashi, Y. Enantioselective conjugate addition of diethylzinc to chalcone catalyzed by chiral Tricarbonyl-(arene)chromium/Nickel(II). Tetrahedron: Asymmetry 1992, 3, 713-714.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 713-714
    • Uemura, M.1    Miyaki, R.2    Nakayama, K.3    Hayashi, Y.4
  • 40
    • 37049090752 scopus 로고
    • Asymmetric synthesis of optically active β-substituted ketones by highly enantioselective catalytic conjugate addition of dialkylzinc reagents to enones using a catalyst system of nickel(II)-chiral ligand-achiral ligand in acetonitrile/toluene
    • (e) Soai, K.; Hayashi, T.; Ugajin, S. Asymmetric synthesis of optically active β-substituted ketones by highly enantioselective catalytic conjugate addition of dialkylzinc reagents to enones using a catalyst system of Nickel(II)-chiral ligand-achiral ligand in acetonitrile/toluene. J. Chem. Soc., Chem. Commun. 1989, 516-517.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 516-517
    • Soai, K.1    Hayashi, T.2    Ugajin, S.3
  • 41
    • 0030908374 scopus 로고    scopus 로고
    • (+)-Camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc
    • (f) De Vries, A. H. M.; Imbos, R.; Feringa, B. L. (+)-Camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc. Tetrahedron: Asymmetry 1997, 8, 1467-1473.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 1467-1473
    • De Vries, A.H.M.1    Imbos, R.2    Feringa, B.L.3
  • 43
    • 0000800084 scopus 로고
    • New chiral ligand for the asymmetric conjugate addition of organocopper reagents to enones
    • (b) Alexakis, A.; Mutti, S.; Normant, J. F. New chiral ligand for the asymmetric conjugate addition of organocopper reagents to enones. J. Am. Chem. Soc. 1991, 113, 6332-6334.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6332-6334
    • Alexakis, A.1    Mutti, S.2    Normant, J.F.3
  • 44
    • 0027135455 scopus 로고
    • Chiral phosphorus ligands for the asymmetric conjugate addition of organocopper reagents
    • Alexakis, A.; Frutos, J.; Mangeney, P. Chiral phosphorus ligands for the asymmetric conjugate addition of organocopper reagents. Tetrahedron: Asymmetry 1993, 4, 2427-2430.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2427-2430
    • Alexakis, A.1    Frutos, J.2    Mangeney, P.3
  • 45
    • 0000836984 scopus 로고
    • Catalytic enantioselective conjugate addition of dialkylzinc compounds to chalcones
    • Bolm, C.; Ewald, M.; Felder, M. Catalytic enantioselective conjugate addition of dialkylzinc compounds to chalcones. Chem. Ber. 1992, 125, 1205-1215.
    • (1992) Chem. Ber. , vol.125 , pp. 1205-1215
    • Bolm, C.1    Ewald, M.2    Felder, M.3
  • 46
    • 0028225036 scopus 로고
    • Enantioselective conjugate addition of diethylzinc to chalcones catalysed by chiral Ni(II) aminoalcohol complexes
    • De Vries, A. H. M.; Jansen, J. F. G. A.; Feringa, B. L. Enantioselective conjugate addition of diethylzinc to chalcones catalysed by chiral Ni(II) aminoalcohol complexes. Tetrahedron 1994, 50, 4479-4491.
    • (1994) Tetrahedron , vol.50 , pp. 4479-4491
    • De Vries, A.H.M.1    Jansen, J.F.G.A.2    Feringa, B.L.3
  • 49
    • 0030477791 scopus 로고    scopus 로고
    • Enantioselective conjugate addition of dialkylzinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites
    • De Vries, A. H. M.; Meetsma, A.; Feringa, B. L. Enantioselective conjugate addition of dialkylzinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites. Angew. Chem., Int. Ed. Engl. 1996, 35, 2374-2376.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2374-2376
    • De Vries, A.H.M.1    Meetsma, A.2    Feringa, B.L.3
  • 51
    • 0034725134 scopus 로고    scopus 로고
    • Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; ligand variation and non-linear effects
    • in press
    • (a) Arnold, L A.; Imbos, R.; Mandoli, A.; de Vries, A. H. M.; Naasz, R.; Feringa, B. L. Enantioselective catalytic conjugate addition of dialkylzinc reagents using copper-phosphoramidite complexes; ligand variation and non-linear effects. Tetrahedron 2000, in press.
    • (2000) Tetrahedron
    • Arnold, L.A.1    Imbos, R.2    Mandoli, A.3    De Vries, A.H.M.4    Naasz, R.5    Feringa, B.L.6
  • 52
    • 0343149693 scopus 로고    scopus 로고
    • New dimeric chiral phosphorus amidites in copper catalyzed asymmetric 1,4-addition of diethylzinc to cyclic α,β-enones; improvement of the enantioselectivity with 2-cyclopentenone
    • in press
    • (b) For recent progress with acyclic enones, see also: Mandoli, A.; Arnold, L. A.; Salvadori, P.; Feringa, B. L New dimeric chiral phosphorus amidites in copper catalyzed asymmetric 1,4-addition of diethylzinc to cyclic α,β-enones; improvement of the enantioselectivity with 2-cyclopentenone. Tetrahedron: Asymmetry 2000, in press.
    • (2000) Tetrahedron: Asymmetry
    • Mandoli, A.1    Arnold, L.A.2    Salvadori, P.3    Feringa, B.L.4
  • 53
    • 0033605762 scopus 로고    scopus 로고
    • Catalytic enantioselective conjugate addition of grignard reagents to cyclic α,β-unsaturated carbonyl compounds
    • For other recent examples, see: (a) Kanai, M.; Nakagawa, Y.; Tomioka, K. Catalytic enantioselective conjugate addition of Grignard reagents to cyclic α,β-unsaturated carbonyl compounds. Tetrahedron 1999, 55, 3843-3854.
    • (1999) Tetrahedron , vol.55 , pp. 3843-3854
    • Kanai, M.1    Nakagawa, Y.2    Tomioka, K.3
  • 54
    • 0032503611 scopus 로고    scopus 로고
    • Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones
    • (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. Rhodium-catalyzed asymmetric 1,4-addition of aryl- and alkenylboronic acids to enones. J. Am. Chem. Soc. 1998, 120, 5579-5580.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5579-5580
    • Takaya, Y.1    Ogasawara, M.2    Hayashi, T.3
  • 55
    • 0033531148 scopus 로고    scopus 로고
    • Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite
    • (c) Yan, M.; Yang, L.-W.; Wong, K.-Y.; Chan, A. S. C. Enantioselective conjugate addition of diethylzinc to enones catalyzed by a copper complex of chiral aryl diphosphite. Chem. Commun. 1999, 11-12.
    • (1999) Chem. Commun. , pp. 11-12
    • Yan, M.1    Yang, L.-W.2    Wong, K.-Y.3    Chan, A.S.C.4
  • 56
    • 0032558607 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL
    • (d) Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphorus ligands derived from TADDOL. Tetrahedron Lett. 1998, 39, 7869-7872.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7869-7872
    • Alexakis, A.1    Vastra, J.2    Burton, J.3    Benhaim, C.4    Mangeney, P.5
  • 57
    • 0033540709 scopus 로고    scopus 로고
    • Catalytic enantioselective annulations via 1,4-addition-Aldol cyclization of functionalized organozinc reagents
    • Naasz, R.; Arnold, L. A.; Pineschi, M.; Keller, E.; Feringa, B. L. Catalytic enantioselective annulations via 1,4-addition-aldol cyclization of functionalized organozinc reagents. J. Am. Chem. Soc. 1999, 121, 1104-1105.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1104-1105
    • Naasz, R.1    Arnold, L.A.2    Pineschi, M.3    Keller, E.4    Feringa, B.L.5
  • 58
    • 84903493491 scopus 로고
    • Preparation of new polyfunctional diorganozincs using a boron-zinc exchange reaction
    • Cf. ref 13d.
    • Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; Knochel, P. Preparation of new polyfunctional diorganozincs using a boron-zinc exchange reaction, Synlett 1994, 410-412. (Cf. ref 13d.)
    • (1994) Synlett , pp. 410-412
    • Langer, F.1    Devasagayaraj, A.2    Chavant, P.-Y.3    Knochel, P.4
  • 59
    • 0000813657 scopus 로고    scopus 로고
    • Enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones using chiral oxazoline-phosphite ligands
    • Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones using chiral oxazoline-phosphite ligands. Synlett 1997, 1429-1431. Cf.: Yan, M.; Chan, A. S. C. Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalysts. Tetrahedron Lett. 1999, 40, 6645.
    • (1997) Synlett , pp. 1429-1431
    • Knöbel, A.K.H.1    Escher, I.H.2    Pfaltz, A.3
  • 60
    • 0033520229 scopus 로고    scopus 로고
    • Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalysts
    • Knöbel, A. K. H.; Escher, I. H.; Pfaltz, A. Enantioselective copper-catalyzed 1,4-addition of organozinc reagents to enones using chiral oxazoline-phosphite ligands. Synlett 1997, 1429-1431. Cf.: Yan, M.; Chan, A. S. C. Enantioselective conjugate addition of diethylzinc to cyclic enones with chiral aryl diphosphite-copper catalysts. Tetrahedron Lett. 1999, 40, 6645.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 6645
    • Yan, M.1    Chan, A.S.C.2
  • 61
    • 0001146718 scopus 로고    scopus 로고
    • Highly enantioselective catalytic conjugate additions to cyclohexadienones
    • Imbos, R.; Brilman, M. H. G.; Pineschi, M.; Feringa, B. L. Highly enantioselective catalytic conjugate additions to cyclohexadienones. Org. Lett. 1999, 1, 623-625.
    • (1999) Org. Lett. , vol.1 , pp. 623-625
    • Imbos, R.1    Brilman, M.H.G.2    Pineschi, M.3    Feringa, B.L.4
  • 62
    • 0030586106 scopus 로고    scopus 로고
    • Conjugate addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system
    • Kitamura, M.; Miki, T.; Nakano, K.; Noyori, R. Conjugate addition of diorganozincs to α,β-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system. Tetrahedron Lett. 1996, 37, 5141-5144.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5141-5144
    • Kitamura, M.1    Miki, T.2    Nakano, K.3    Noyori, R.4
  • 63
    • 0032540965 scopus 로고    scopus 로고
    • Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands
    • Keller, E.; Maurer, J.; Naasz, R.; Schrader, T.; Meetsma, A.; Feringa, B. L. Unexpected enhancement of enantioselectivity in copper(II) catalyzed conjugate addition of diethylzinc to cyclic enones with novel TADDOL phosphorus amidite ligands. Tetrahedron: Asymmetry 1998, 9, 2409-2413.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2409-2413
    • Keller, E.1    Maurer, J.2    Naasz, R.3    Schrader, T.4    Meetsma, A.5    Feringa, B.L.6
  • 64
    • 33847804003 scopus 로고
    • Asymmetric synthesis of bicyclic intermediates of natural product chemistry
    • Hajos, Z. G.; Parrish, D. R. Asymmetric synthesis of bicyclic intermediates of natural product chemistry. J. Org. Chem. 1974, 39, 1615-1621.
    • (1974) J. Org. Chem. , vol.39 , pp. 1615-1621
    • Hajos, Z.G.1    Parrish, D.R.2
  • 65
    • 0033618260 scopus 로고    scopus 로고
    • Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes
    • (a) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L Copper(I) phosphoramidite catalyzed asymmetric conjugate addition of dialkylzinc reagents to α,β-unsaturated nitroacetates; an enantioselective route to β-aryl-nitroalkanes. Tetrahedron Lett. 1999, 40, 5803-5806.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5803-5806
    • Versleijen, J.P.G.1    Van Leusen, A.M.2    Feringa, B.L.3
  • 66
    • 0032562674 scopus 로고    scopus 로고
    • Enantioselective copper-(I) catalyzed 1,4-addition of diethylzinc to nitroolefins
    • (b) Sewald, N.; Wendisch, V. Enantioselective copper-(I) catalyzed 1,4-addition of diethylzinc to nitroolefins. Tetrahedron: Asymmetry 1998, 9, 1341-1344.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 1341-1344
    • Sewald, N.1    Wendisch, V.2
  • 67
    • 0001245686 scopus 로고    scopus 로고
    • Alkylations of functionalised organozinc reagents with allylic epoxides catalysed by a cyanocuprate
    • Lipshutz, B. H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. Alkylations of functionalised organozinc reagents with allylic epoxides catalysed by a cyanocuprate. Synlett 1997, 477-478.
    • (1997) Synlett , pp. 477-478
    • Lipshutz, B.H.1    Woo, K.2    Gross, T.3    Buzard, D.J.4    Tirado, R.5
  • 68
    • 0032532776 scopus 로고    scopus 로고
    • Catalytic enantioselective carbon-carbon bond formation by addition of dialkylzinc reagents to cyclic 1,3-diene monoepoxides
    • Badalassi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, L. A.; Feringa, B. L. Catalytic enantioselective carbon-carbon bond formation by addition of dialkylzinc reagents to cyclic 1,3-diene monoepoxides. Tetrahedron Lett. 1998, 39, 7795-7798.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 7795-7798
    • Badalassi, F.1    Crotti, P.2    Macchia, F.3    Pineschi, M.4    Arnold, L.A.5    Feringa, B.L.6
  • 69
    • 0033603476 scopus 로고    scopus 로고
    • A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into α-allenic alcohols
    • Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, L. A.; Feringa, B. L. A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into α-allenic alcohols. Tetrahedron Lett. 1999, 40, 4893-4896.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4893-4896
    • Bertozzi, F.1    Crotti, P.2    Macchia, F.3    Pineschi, M.4    Arnold, L.A.5    Feringa, B.L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.