메뉴 건너뛰기




Volumn 55, Issue 17, 2010, Pages 1712-1722

Asymmetric epoxidation of α,β-unsaturated ketones using α,α-diarylprolinols as catalysts

Author keywords

Electron deficient olefins; Epoxidation; Ketone; Organocatalysis; Prolinol

Indexed keywords


EID: 77953887260     PISSN: 10016538     EISSN: 18619541     Source Type: Journal    
DOI: 10.1007/s11434-010-3129-0     Document Type: Review
Times cited : (6)

References (31)
  • 1
    • 0037124555 scopus 로고    scopus 로고
    • A critical outlook and comparison of enantioselective oxidation methodologies of olefins
    • Bonini C, Righi G. A critical outlook and comparison of enantioselective oxidation methodologies of olefins. Tetrahedron, 2002, 58: 4981-5021.
    • (2002) Tetrahedron , vol.58 , pp. 4981-5021
    • Bonini, C.1    Righi, G.2
  • 3
    • 22744455748 scopus 로고    scopus 로고
    • Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model
    • Zhang W, Basak A, Kosugi Y, et al. Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model. Angew Chem Int Ed, 2005, 44: 4389-4391.
    • (2005) Angew Chem Int Ed , vol.44 , pp. 4389-4391
    • Zhang, W.1    Basak, A.2    Kosugi, Y.3
  • 4
    • 33846214050 scopus 로고    scopus 로고
    • Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols
    • Zhang W, Yamamoto H. Vanadium-catalyzed asymmetric epoxidation of homoallylic alcohols. J Am Chem Soc, 2007, 129: 286-287.
    • (2007) J Am Chem Soc , vol.129 , pp. 286-287
    • Zhang, W.1    Yamamoto, H.2
  • 5
    • 20344404984 scopus 로고    scopus 로고
    • Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation
    • Xia Q H, Ge H Q, Ye C P, et al. Advances in homogeneous and heterogeneous catalytic asymmetric epoxidation. Chem Rev, 2005, 105: 1603-1662.
    • (2005) Chem Rev , vol.105 , pp. 1603-1662
    • Xia, Q.H.1    Ge, H.Q.2    Ye, C.P.3
  • 6
    • 44349148129 scopus 로고    scopus 로고
    • Selective oxidation of aliphatic C-H bonds in the synthesis of complex molecules
    • Christmann M. Selective oxidation of aliphatic C-H bonds in the synthesis of complex molecules. Angew Chem Int Ed, 2008, 47: 2740-2742.
    • (2008) Angew Chem Int Ed , vol.47 , pp. 2740-2742
    • Christmann, M.1
  • 7
    • 4143088133 scopus 로고    scopus 로고
    • Organocatalytic asymmetric epoxidation of olefins by chiral ketones
    • Shi Y. Organocatalytic asymmetric epoxidation of olefins by chiral ketones. Acc Chem Res, 2004, 37: 488-496.
    • (2004) Acc Chem Res , vol.37 , pp. 488-496
    • Shi, Y.1
  • 8
    • 0035526027 scopus 로고    scopus 로고
    • Synthetic applications of nonmetal catalysts for homogeneous oxidations
    • Adam W, Saha-Möller C R, Ganeshpure P A. Synthetic applications of nonmetal catalysts for homogeneous oxidations. Chem Rev, 2001, 101: 3499-3548.
    • (2001) Chem Rev , vol.101 , pp. 3499-3548
    • Adam, W.1    Saha-Möller, C.R.2    Ganeshpure, P.A.3
  • 9
    • 33744782373 scopus 로고    scopus 로고
    • Catalytic asymmetric epoxidation of α, β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors
    • Matsunaga S, Qin H, Sugita M, et al. Catalytic asymmetric epoxidation of α, β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors. Tetrahedron, 2006, 62: 6630-6639.
    • (2006) Tetrahedron , vol.62 , pp. 6630-6639
    • Matsunaga, S.1    Qin, H.2    Sugita, M.3
  • 10
    • 85178435883 scopus 로고
    • The impact of alkali hydrogen superoxyde on unsaturated compounds
    • Weitz E, Scheffer A. The impact of alkali hydrogen superoxyde on unsaturated compounds. Ber Dtsch Chem Ges, 1921, 54: 2327-2344.
    • (1921) Ber Dtsch Chem Ges , vol.54 , pp. 2327-2344
    • Weitz, E.1    Scheffer, A.2
  • 11
    • 0001461245 scopus 로고
    • Catalytic asymmetric induction in oxidation reactions-synthesis of optically-active epoxynaphthoquinones
    • Pluim H, Wynberg H. Catalytic asymmetric induction in oxidation reactions-synthesis of optically-active epoxynaphthoquinones. J Org Chem, 1980, 45: 2498-2502.
    • (1980) J Org Chem , vol.45 , pp. 2498-2502
    • Pluim, H.1    Wynberg, H.2
  • 12
    • 37049095864 scopus 로고
    • Synthetic enzymes. 2. catalytic asymmetric epoxidation by means of polyamino-acids in a triphase system
    • Juliá S, Guixer J, Masana J, et al. Synthetic enzymes. 2. catalytic asymmetric epoxidation by means of polyamino-acids in a triphase system. J Chem Soc Perkin Trans 1, 1982, 6: 1317-1324.
    • (1982) J Chem Soc Perkin Trans 1 , vol.6 , pp. 1317-1324
    • Juliá, S.1    Guixer, J.2    Masana, J.3
  • 13
    • 28544451072 scopus 로고    scopus 로고
    • Enantioselective epoxidation of α, β-enones promoted by α, α-diphenyl-L-prolinol as bifunctional organocatalyst
    • Lattanzi A. Enantioselective epoxidation of α, β-enones promoted by α, α-diphenyl-L-prolinol as bifunctional organocatalyst. Org Lett, 2005, 7: 2579-2582.
    • (2005) Org Lett , vol.7 , pp. 2579-2582
    • Lattanzi, A.1
  • 14
    • 33645763521 scopus 로고    scopus 로고
    • Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones
    • Liu X Y, Li Y W, Wang G Y, et al. Effective and recyclable dendritic ligands for the enantioselective epoxidation of enones. Tetrahedron: Asymmetry, 2006, 17: 750-755.
    • (2006) Tetrahedron: Asymmetry , vol.17 , pp. 750-755
    • Liu, X.Y.1    Li, Y.W.2    Wang, G.Y.3
  • 15
    • 0036810318 scopus 로고    scopus 로고
    • Dendrimers as support for recoverable catalysts and reagents
    • van Heerbeek R, Kamer P C J, van Leeuwen P W N M, et al. Dendrimers as support for recoverable catalysts and reagents. Chem Rev, 2002, 102: 3717-3756.
    • (2002) Chem Rev , vol.102 , pp. 3717-3756
    • van Heerbeek, R.1    Kamer, P.C.J.2    van Leeuwen, P.W.N.M.3
  • 16
    • 0036738404 scopus 로고    scopus 로고
    • The use of ultra- and nanofiltration techniques in homogeneous catalyst recycling
    • Dijkstra H P, van Klink G P M, van Koten G. The use of ultra- and nanofiltration techniques in homogeneous catalyst recycling. Acc Chem Res, 2002, 35: 798-810.
    • (2002) Acc Chem Res , vol.35 , pp. 798-810
    • Dijkstra, H.P.1    van Klink, G.P.M.2    van Koten, G.3
  • 17
    • 0034616491 scopus 로고    scopus 로고
    • Fan Q H, Chen Y M, Chen X M, et al. Highly effective and recyclable dendritic BINAP ligands for asymmetric hydrogenation. Chem Commun, 2000, 789-790.
  • 18
    • 24144492691 scopus 로고    scopus 로고
    • Highly effective and recyclable dendritic ligands for the enantioselective aryl transfer reactions to aldehydes
    • Liu X Y, Wu X Y, Chai Z, et al. Highly effective and recyclable dendritic ligands for the enantioselective aryl transfer reactions to aldehydes. J Org Chem, 2005, 70: 7432-7435.
    • (2005) J Org Chem , vol.70 , pp. 7432-7435
    • Liu, X.Y.1    Wu, X.Y.2    Chai, Z.3
  • 19
    • 33644606047 scopus 로고    scopus 로고
    • Bis(3,5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol: An improved organocatalyst for the asymmetric epoxidation of α, β-enones
    • Lattanzi A. Bis(3, 5-dimethylphenyl)-(S)-pyrrolidin-2-ylmethanol: An improved organocatalyst for the asymmetric epoxidation of α, β-enones. Adv Synth Catal, 2006, 348: 339-346.
    • (2006) Adv Synth Catal , vol.348 , pp. 339-346
    • Lattanzi, A.1
  • 20
    • 33750951722 scopus 로고    scopus 로고
    • Diaryl-2-pyrrolidinemethanols catalyzed enantioselective epoxidation of α, β-enones: New insight into the effect of structural modification of the catalyst on reaction efficiency
    • Lattanzi A, Russo A. Diaryl-2-pyrrolidinemethanols catalyzed enantioselective epoxidation of α, β-enones: New insight into the effect of structural modification of the catalyst on reaction efficiency. Tetrahedron, 2006, 62: 12264-12269.
    • (2006) Tetrahedron , vol.62 , pp. 12264-12269
    • Lattanzi, A.1    Russo, A.2
  • 21
    • 33846069767 scopus 로고    scopus 로고
    • 4-Substituted-α, α-diaryl-prolinols improve the enantioselective catalytic epoxidation of α, β-enones
    • Li Y W, Liu X Y, Zhao G. 4-Substituted-α, α-diaryl-prolinols improve the enantioselective catalytic epoxidation of α, β-enones. J Org Chem, 2007, 72: 288-291.
    • (2007) J Org Chem , vol.72 , pp. 288-291
    • Li, Y.W.1    Liu, X.Y.2    Zhao, G.3
  • 22
    • 67650472198 scopus 로고    scopus 로고
    • Highly efficient asymmetric epoxidation of electron-deficient α, β-enones and related applications to organic synthesis
    • Zheng C W, Li Y W, Yang Y Q, et al. Highly efficient asymmetric epoxidation of electron-deficient α, β-enones and related applications to organic synthesis. Adv Synth Catal, 2009, 351: 1685-1691.
    • (2009) Adv Synth Catal , vol.351 , pp. 1685-1691
    • Zheng, C.W.1    Li, Y.W.2    Yang, Y.Q.3
  • 23
    • 77953894753 scopus 로고    scopus 로고
    • Buschmann H H, Antoni T J, Susana Y M, et al. PCT Int Appl 2007 WO 2007000329.
  • 24
    • 34548062694 scopus 로고    scopus 로고
    • Design, synthesis, and in vivo SAR of a novel series of pyrazolines as potent selective androgen receptor modulators
    • Zhang X Q, Li X J, Allan G F, et al. Design, synthesis, and in vivo SAR of a novel series of pyrazolines as potent selective androgen receptor modulators. J Med Chem, 2007, 50: 3857-3869.
    • (2007) J Med Chem , vol.50 , pp. 3857-3869
    • Zhang, X.Q.1    Li, X.J.2    Allan, G.F.3
  • 25
    • 33845183051 scopus 로고
    • Aminolysis of 2,2,2-trichloro-1-arylethanones in aprotic solvents
    • Druzian J, Zucco C, Rezende M C, et al. Aminolysis of 2, 2, 2-trichloro-1-arylethanones in aprotic solvents. J Org Chem, 1989, 54: 4767-4771.
    • (1989) J Org Chem , vol.54 , pp. 4767-4771
    • Druzian, J.1    Zucco, C.2    Rezende, M.C.3
  • 26
    • 48849106483 scopus 로고    scopus 로고
    • Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids
    • Yang L, Zheng Q Y, Wang D X, et al. Reversal of nucleophilicity of enamides in water: Control of cyclization pathways by reaction media for the orthogonal synthesis of dihydropyridinone and pyrrolidinone Clausena alkaloids. Org Lett, 2008, 10: 2461-2464.
    • (2008) Org Lett , vol.10 , pp. 2461-2464
    • Yang, L.1    Zheng, Q.Y.2    Wang, D.X.3
  • 27
    • 35348950676 scopus 로고    scopus 로고
    • Johansen M B, Leduc A B, Kerr M A. Concise biomimetic total syntheses of both antipodes of balasubramide. Synlett, 2007, 2593-2595.
  • 28
    • 0028883110 scopus 로고
    • Stereoselective reduction of alpha,beta-epoxy ketones with sodium-borohydride in the presence of calcium-chloride or lanthanum chloride-a practical preparation of erythro-α, β-epoxy alcohols
    • Taniguchi M, Fujii H, Oshima K, et al. Stereoselective reduction of alpha, beta-epoxy ketones with sodium-borohydride in the presence of calcium-chloride or lanthanum chloride-a practical preparation of erythro-α, β-epoxy alcohols. Tetrahedron, 1995, 51: 679-686.
    • (1995) Tetrahedron , vol.51 , pp. 679-686
    • Taniguchi, M.1    Fujii, H.2    Oshima, K.3
  • 29
    • 26444544195 scopus 로고    scopus 로고
    • Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone
    • Yadav J S, Raju A K, Rao P P, et al. Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone. Tetrahedron: Asymmetry, 2005, 16: 3283-3290.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3283-3290
    • Yadav, J.S.1    Raju, A.K.2    Rao, P.P.3
  • 30
    • 34548525558 scopus 로고    scopus 로고
    • Epoxide-opening cascades promoted by water
    • Vilotijevic I, Jamison T F. Epoxide-opening cascades promoted by water. Science, 2007, 317: 1189-1192.
    • (2007) Science , vol.317 , pp. 1189-1192
    • Vilotijevic, I.1    Jamison, T.F.2
  • 31
    • 33845553525 scopus 로고
    • Carbonyl ylides from aldehydes and carbenes
    • Pedro de M, Rolf H. Carbonyl ylides from aldehydes and carbenes. J Am Chem Soc, 1982, 104: 4952.
    • (1982) J Am Chem Soc , vol.104 , pp. 4952
    • de Pedro, M.1    Rolf, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.