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Volumn 17, Issue 8, 2012, Pages 9010-9022

Chiral Zn(II)-bisamidine complex as a lewis-brønsted combined acid catalyst: Application to asymmetric mukaiyama aldol reactions of α-ketoesters

Author keywords

ketoester; Asymmetric Mukaiyama aldol reaction; Bisamidine; Lewis Br nsted combined acid

Indexed keywords

ESTER; ETHER DERIVATIVE; LEWIS ACID; ORGANOMETALLIC COMPOUND; SILANE DERIVATIVE; SOLVENT; SUCCINIC ACID DERIVATIVE; TRIFLUOROETHANOL; ZINC;

EID: 84865445637     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17089010     Document Type: Article
Times cited : (16)

References (38)
  • 1
    • 16844374787 scopus 로고    scopus 로고
    • Designer acids™: Combined acid catalysis for asymmetric synthesis
    • Yamamoto, H.; Futatsugi, K. "Designer acids™: Combined acid catalysis for asymmetric synthesis. Angew. Chem. Int. Ed. Engl. 2005, 44, 1924-1942.
    • (2005) Angew. Chem. Int. Ed. Engl. , vol.44 , pp. 1924-1942
    • Yamamoto, H.1    Futatsugi, K.2
  • 2
    • 0022522973 scopus 로고
    • Asymmetric Diels-Alder reaction directed toward chiral anthracycline intermediates
    • Maruoka, K.; Sakurai, M.; Fujiwara, J.; Yamamoto, H. Asymmetric Diels-Alder reaction directed toward chiral anthracycline intermediates. Tetrahedron 1986, 27, 4895-4898.
    • (1986) Tetrahedron , vol.27 , pp. 4895-4898
    • Maruoka, K.1    Sakurai, M.2    Fujiwara, J.3    Yamamoto, H.4
  • 3
    • 0000224603 scopus 로고
    • Acyloxyborane: An activating device for carboxylic acids
    • Furuta, K.; Miwa, Y.; Iwanaga, K.; Yamamoto, H. Acyloxyborane: An activating device for carboxylic acids. J. Am. Chem. Soc. 1988, 110, 6254-6255.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 6254-6255
    • Furuta, K.1    Miwa, Y.2    Iwanaga, K.3    Yamamoto, H.4
  • 4
    • 0000656506 scopus 로고
    • A new chiral BLA promoter for asymmetric aza Diels-Alder and Aldol-type reactions of imines
    • Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H.Y. A new chiral BLA promoter for asymmetric aza Diels-Alder and Aldol-type reactions of imines. J. Am. Chem. Soc. 1994, 116, 10520-10524.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 10520-10524
    • Ishihara, K.1    Miyata, M.2    Hattori, K.3    Tada, T.4    Yamamoto, H.Y.5
  • 5
    • 0000778261 scopus 로고
    • Brønsted acid assisted chiral Lewis acid (BLA) catalyst for asymmetric Diels-Alder reaction
    • Ishihara, K.; Yamamoto, H. Brønsted acid assisted chiral Lewis acid (BLA) catalyst for asymmetric Diels-Alder reaction. J. Am. Chem. Soc. 1994, 116, 1561-1562.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1561-1562
    • Ishihara, K.1    Yamamoto, H.2
  • 6
    • 0000358324 scopus 로고    scopus 로고
    • A new powerful and practical BLA catalyst for highly enantioselective Diels-Alder reaction: An extreme acceleration of reaction rate by Brønsted acid
    • Ishihara, K.; Kurihara, H.; Yamamoto, H. A new powerful and practical BLA catalyst for highly enantioselective Diels-Alder reaction: An extreme acceleration of reaction rate by Brønsted acid. J. Am. Chem. Soc. 1996, 118, 3049-3050.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3049-3050
    • Ishihara, K.1    Kurihara, H.2    Yamamoto, H.3
  • 7
    • 0032558078 scopus 로고    scopus 로고
    • Design of Brønsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions
    • Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. Design of Brønsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels-Alder reactions. J. Am. Chem. Soc. 1998, 120, 6920-6930.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6920-6930
    • Ishihara, K.1    Kurihara, H.2    Matsumoto, M.3    Yamamoto, H.4
  • 8
    • 0037123222 scopus 로고    scopus 로고
    • Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine
    • Corey, E.J.; Shibata, T.; Lee, T.W. Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine. J. Am. Chem. Soc. 2002, 124, 3808-3809.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3808-3809
    • Corey, E.J.1    Shibata, T.2    Lee, T.W.3
  • 9
    • 0037190055 scopus 로고    scopus 로고
    • Broad-spectrum enantioselective Diels-Alder catalysis by chiral, cationic oxazaborolidines
    • Ryu, D.H.; Lee, T.W.; Corey, E.J. Broad-spectrum enantioselective Diels-Alder catalysis by chiral, cationic oxazaborolidines. J. Am. Chem. Soc. 2002, 124, 9992-9993.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9992-9993
    • Ryu, D.H.1    Lee, T.W.2    Corey, E.J.3
  • 10
    • 0038514123 scopus 로고    scopus 로고
    • Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition
    • Ryu, D.H.; Corey, E.J. Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition. J. Am. Chem. Soc. 2003, 125, 6388-6390.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6388-6390
    • Ryu, D.H.1    Corey, E.J.2
  • 11
    • 34547752028 scopus 로고    scopus 로고
    • Regioselective and asymmetric Diels-Alder reaction of 1- and 2-substituted cyclopentadienes catalyzed by a Brønsted acid activated chiral oxazaborolidine
    • Payette, J.N.; Yamamoto, H. Regioselective and asymmetric Diels-Alder reaction of 1- and 2-substituted cyclopentadienes catalyzed by a Brønsted acid activated chiral oxazaborolidine. J. Am. Chem. Soc. 2007, 129, 9536-9537.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9536-9537
    • Payette, J.N.1    Yamamoto, H.2
  • 12
    • 70350676812 scopus 로고    scopus 로고
    • Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction
    • Hu, G.; Huang, L.; Huang, R.H.; Wulff, W.D. Evidence for a boroxinate based Brønsted acid derivative of VAPOL as the active catalyst in the catalytic asymmetric aziridination reaction. J. Am. Chem. Soc. 2009, 131, 15615-15617.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 15615-15617
    • Hu, G.1    Huang, L.2    Huang, R.H.3    Wulff, W.D.4
  • 13
    • 66249089488 scopus 로고    scopus 로고
    • Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope
    • Rauniyar, V.; Hall, D.G. Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope. J. Org. Chem. 2009, 74, 4236-4241.
    • (2009) J. Org. Chem. , vol.74 , pp. 4236-4241
    • Rauniyar, V.1    Hall, D.G.2
  • 14
    • 77749249116 scopus 로고    scopus 로고
    • Asymmetric binary-acid catalysis with chiral phosphoric acid and MgF2: Catalytic enantioselective Friedel-Crafts reactions of β,γ- unsaturated α-ketoesters
    • Lv, J.; Li, X.; Zhong, L.; Luo, S.; Cheng, J.-P. Asymmetric binary-acid catalysis with chiral phosphoric acid and MgF2: catalytic enantioselective Friedel-Crafts reactions of β,γ-unsaturated α-ketoesters. Org. Lett. 2010, 12, 1096-1099.
    • (2010) Org. Lett. , vol.12 , pp. 1096-1099
    • Lv, J.1    Li, X.2    Zhong, L.3    Luo, S.4    Cheng, J.-P.5
  • 15
    • 1642369984 scopus 로고    scopus 로고
    • Chiral proton catalysis: A catalytic enantioselective direct Aza-Henry reaction
    • Nugent, B.M.; Yoder, R.A.; Johnston, J.N. Chiral proton catalysis: A catalytic enantioselective direct Aza-Henry reaction. J. Am. Chem. Soc. 2004, 126, 3418-3419.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 3418-3419
    • Nugent, B.M.1    Yoder, R.A.2    Johnston, J.N.3
  • 16
    • 33947648877 scopus 로고    scopus 로고
    • Chiral proton catalysis: Enantioselective Brønsted acid catalyzed additions of nitroacetic acid derivatives as glycine equivalents
    • Singh, A.; Yoder, R.A.; Shen, B.; Johnston, J.N. Chiral proton catalysis: Enantioselective Brønsted acid catalyzed additions of nitroacetic acid derivatives as glycine equivalents. J. Am. Chem. Soc. 2007, 129, 3466-3467.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 3466-3467
    • Singh, A.1    Yoder, R.A.2    Shen, B.3    Johnston, J.N.4
  • 17
    • 77950449031 scopus 로고    scopus 로고
    • Bifunctional asymmetric catalysis: Amplification of Brønsted basicity can orthogonally increase the reactivity of a chiral Brønsted acid
    • Davis, T.A.; Wilt, J.C.; Johnston, J.N. Bifunctional asymmetric catalysis: Amplification of Brønsted basicity can orthogonally increase the reactivity of a chiral Brønsted acid. J. Am. Chem. Soc. 2010, 132, 2880-2882.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 2880-2882
    • Davis, T.A.1    Wilt, J.C.2    Johnston, J.N.3
  • 18
    • 34547124050 scopus 로고    scopus 로고
    • Synthesis of c2-symmetric bisamidines: A new type of chiral metal-free lewis acid analogue interacting with carbonyl groups
    • Akalay, D.; Dürner, G.; Bats, J.W.; Bolte, M.; Göbel, M.W. Synthesis of C2-Symmetric Bisamidines: A New Type of Chiral Metal-Free Lewis Acid Analogue Interacting with Carbonyl Groups. J. Org. Chem. 2007, 72, 5618-5624.
    • (2007) J. Org. Chem. , vol.72 , pp. 5618-5624
    • Akalay, D.1    Dürner, G.2    Bats, J.W.3    Bolte, M.4    Göbel, M.W.5
  • 19
    • 79952574780 scopus 로고    scopus 로고
    • C2-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones
    • doi:10.3762/bjoc.4.28
    • Akalay, D.; Dürner, G.; Bats, J. W.; Göbel, M.W. C2-symmetric bisamidines: Chiral Brønsted bases catalysing the Diels-Alder reaction of anthrones. Beilstein J. Org. Chem. 2008, 4, doi:10.3762/bjoc.4.28.
    • (2008) Beilstein J. Org. Chem. , vol.4
    • Akalay, D.1    Dürner, G.2    Bats, J.W.3    Göbel, M.W.4
  • 20
    • 79955672250 scopus 로고    scopus 로고
    • A chiral bidentate sp2-N ligand, Naph-diPIM: Application to CpRu-catalyzed asymmetric dehydrative C-, N-, and O-allylation
    • Miyata, K.; Kutsuna, H.; Kawakami, S.; Kitamura, M. A Chiral Bidentate sp2-N Ligand, Naph-diPIM: Application to CpRu-Catalyzed Asymmetric Dehydrative C-, N-, and O-Allylation. Angew. Chem. Int. Ed. Engl. 2011, 50, 4649-4653.
    • (2011) Angew. Chem. Int. Ed. Engl. , vol.50 , pp. 4649-4653
    • Miyata, K.1    Kutsuna, H.2    Kawakami, S.3    Kitamura, M.4
  • 21
    • 67650657513 scopus 로고    scopus 로고
    • Catalytic enantioselective aldol additions to ketones
    • Catalytic enantioselective aldol additions to ketones
    • Catalytic enantioselective aldol additions to ketones, see: Adachi, S.; Harada, T. Catalytic Enantioselective Aldol additions to ketones. Eur. J. Org. Chem. 2009, 3661-3671.
    • (2009) Eur. J. Org. Chem. , pp. 3661-3671
    • Adachi, S.1    Harada, T.2
  • 22
    • 0030952586 scopus 로고    scopus 로고
    • C2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
    • Evans, D.A.; Kozlowski, M.C.; Burgey, C.S.; MacMillan, D.W.C. C2-symmetric copper(II) complexes as chiral Lewis acids. Catalytic enantioselective aldol additions of enolsilanes to pyruvate esters. J. Am. Chem. Soc. 1997, 119, 7893-7894.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7893-7894
    • Evans, D.A.1    Kozlowski, M.C.2    Burgey, C.S.3    MacMillan, D.W.C.4
  • 23
    • 0030781007 scopus 로고    scopus 로고
    • C2-Symmetric tin(II) complexes as chiral Lewis acids. Catalytic enantioselective anti aldol additions of enolsilanes to glyoxylate and pyruvate esters
    • Evans, D.A.; MacMillan, D.W.C.; Campos, K.R. C2-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, 10859-10860.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10859-10860
    • Evans, D.A.1    MacMillan, D.W.C.2    Campos, K.R.3
  • 24
    • 0033518571 scopus 로고    scopus 로고
    • C2-Symmetric copper(II) complexes as chiral Lewis acids. Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters
    • Evans, D.A.; Burgey, C.S.; Kozlowski, M.C.; Tregay, S.W. C2-Symmetric copper(II) complexes as chiral Lewis acids. Scope and mechanism of the catalytic enantioselective aldol additions of enolsilanes to pyruvate esters. J. Am. Chem. Soc. 1999, 121, 686-699.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 686-699
    • Evans, D.A.1    Burgey, C.S.2    Kozlowski, M.C.3    Tregay, S.W.4
  • 25
    • 9244221087 scopus 로고    scopus 로고
    • C1-Symmetric sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama-type aldol reactions
    • Langner, M.; Bolm, C. C1-Symmetric sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama-type aldol reactions. Angew. Chem. Int. Ed. Engl. 2004, 43, 5984-5987.
    • (2004) Angew. Chem. Int. Ed. Engl. , vol.43 , pp. 5984-5987
    • Langner, M.1    Bolm, C.2
  • 26
    • 58149186445 scopus 로고    scopus 로고
    • C1-Symmetric oxazolinyl sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama aldol reactions
    • Sedelmeier, J.; Hammerer, T.; Bolm, C. C1-Symmetric oxazolinyl sulfoximines as ligands in copper-catalyzed asymmetric Mukaiyama aldol reactions. Org. Lett. 2008, 10, 917-920.
    • (2008) Org. Lett. , vol.10 , pp. 917-920
    • Sedelmeier, J.1    Hammerer, T.2    Bolm, C.3
  • 27
    • 33646746416 scopus 로고    scopus 로고
    • A chiral Ag-based catalyst for practical, efficient, and highly enantioselective additions of enolsilanes to α-ketoesters
    • Akullian, L.C.; Snapper, M.L.; Hoveyda, A.H. A chiral Ag-based catalyst for practical, efficient, and highly enantioselective additions of enolsilanes to α-ketoesters. J. Am. Chem. Soc. 2006, 128, 6532-6533.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6532-6533
    • Akullian, L.C.1    Snapper, M.L.2    Hoveyda, A.H.3
  • 28
    • 71549172794 scopus 로고    scopus 로고
    • A general asymmetric aldol reaction of silyl ketene acetals derived from simple esters to aryl α-keto esters
    • Engers, J.L.; Pagenkopf, B.L. A general asymmetric aldol reaction of silyl ketene acetals derived from simple esters to aryl α-keto esters. Eur. J. Org. Chem. 2009, 6109-6111.
    • (2009) Eur. J. Org. Chem. , pp. 6109-6111
    • Engers, J.L.1    Pagenkopf, B.L.2
  • 29
    • 4444329099 scopus 로고    scopus 로고
    • Efficient mukaiyama aldol reaction by silver (i) carboxylate- bis(phosphine) catalysts
    • Ohkouchi, M.; Masui, D.; Yamaguchi, M.; Yamagishi, T. Efficient Mukaiyama aldol reaction by silver(I) carboxylate-bis(phosphine) catalysts. Nippon Kagaku Kaishi 2002, 223-229.
    • (2002) Nippon Kagaku Kaishi , pp. 223-229
    • Ohkouchi, M.1    Masui, D.2    Yamaguchi, M.3    Yamagishi, T.4
  • 30
    • 73149104665 scopus 로고    scopus 로고
    • Enantioselective total synthesis of (-)-Acylfulvene and (-)-Irofulven
    • Synthesis of α-hydroxyester having sequential quarternary carbons by asymmetric Mukaiyama aldol reaction of methyl pyruvate and cyclopropyl silylketenehemithioacetal
    • Synthesis of α-hydroxyester having sequential quarternary carbons by asymmetric Mukaiyama aldol reaction of methyl pyruvate and cyclopropyl silylketenehemithioacetal, see: Siegel, D.S.; Piizzi, G.; Piersanti, G.; Movassaghi, M. Enantioselective total synthesis of (-)-Acylfulvene and (-)-Irofulven. J. Org. Chem. 2009, 74, 9292-9304.
    • (2009) J. Org. Chem. , vol.74 , pp. 9292-9304
    • Siegel, D.S.1    Piizzi, G.2    Piersanti, G.3    Movassaghi, M.4
  • 32
    • 0345711474 scopus 로고    scopus 로고
    • Towards perfect asymmetric catalysis: Additives and cocatalysts
    • Vogl, E.M.; Gröger, H.; Shibasaki, M. Towards perfect asymmetric catalysis: Additives and cocatalysts. Angew. Chem. Int. Ed. Engl. 1999, 38, 1570-1577.
    • (1999) Angew. Chem. Int. Ed. Engl. , vol.38 , pp. 1570-1577
    • Vogl, E.M.1    Gröger, H.2    Shibasaki, M.3
  • 33
    • 0033541094 scopus 로고    scopus 로고
    • C2-Symmetric Cu(II) complexes as chiral Lewis acids. Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates
    • Evans, D.A.; Rovis, T.; Kozlowski, M.C.; Tedrow, J.S. C2-Symmetric Cu(II) complexes as chiral Lewis acids. Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates. J. Am. Chem. Soc. 1999, 121, 1994-1995.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1994-1995
    • Evans, D.A.1    Rovis, T.2    Kozlowski, M.C.3    Tedrow, J.S.4
  • 34
    • 0033598250 scopus 로고    scopus 로고
    • Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes
    • Evans, D.A.; Willis, M.C.; Johnston, J.N. Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes. Org. Lett. 1999, 1, 865-868.
    • (1999) Org. Lett. , vol.1 , pp. 865-868
    • Evans, D.A.1    Willis, M.C.2    Johnston, J.N.3
  • 35
    • 35348986604 scopus 로고    scopus 로고
    • Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis
    • Shuklov, I.A.; Dubrovina, N.V.; Börner, A. Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis. Synthesis 2007, 2925-2943.
    • (2007) Synthesis , pp. 2925-2943
    • Shuklov, I.A.1    Dubrovina, N.V.2    Börner, A.3
  • 36
    • 27144522622 scopus 로고    scopus 로고
    • Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins
    • Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefins. Org. Lett. 2005, 21, 4713-4716.
    • (2005) Org. Lett. , vol.21 , pp. 4713-4716
    • Wang, J.1    Li, H.2    Duan, W.3    Zu, L.4    Wang, W.5
  • 37
    • 0029743317 scopus 로고    scopus 로고
    • An improved catalyst system for aromatic carbon-nitrogen bond formation: The possible involvement of bis(phosphine) palladium complexes as key intermediates
    • Wolfe, J.P.; Wagaw, S.; Buchwald, S.L. An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates. J. Am. Chem. Soc. 1996, 118, 7215-7216.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7215-7216
    • Wolfe, J.P.1    Wagaw, S.2    Buchwald, S.L.3
  • 38
    • 0034125886 scopus 로고    scopus 로고
    • Ruthenium(II) and palladium(II) complexes mediated addition of ketene silyl ketal to aldehydes and ketones: Remarkable influence of the nature of the ligand
    • Doucet, H.; Parrain, J.-L.; Santelli, M. Ruthenium(II) and palladium(II) complexes mediated addition of ketene silyl ketal to aldehydes and ketones: Remarkable influence of the nature of the ligand. Synlett 2000, 871-873.
    • (2000) Synlett , pp. 871-873
    • Doucet, H.1    Parrain, J.-L.2    Santelli, M.3


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