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Volumn 12, Issue 9, 2007, Pages 2089-2105

Aqueous Barbier allylation of aldehydes mediated by tin

Author keywords

Aqueous; Fast Barbier reaction; Hydroxy and methoxy benzaldehydes; Tin

Indexed keywords


EID: 34848901336     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12092089     Document Type: Article
Times cited : (18)

References (47)
  • 1
    • 0029975056 scopus 로고    scopus 로고
    • Aqueous Barbier-Grignard Type Reaction: Scope, Mechanism, and Synthetic Applications
    • (a) Li, C. J. Aqueous Barbier-Grignard Type Reaction: Scope, Mechanism, and Synthetic Applications. Tetrahedron, 1996, 52, 5643-5668;
    • (1996) Tetrahedron , vol.52 , pp. 5643-5668
    • Li, C.J.1
  • 3
    • 0037433608 scopus 로고    scopus 로고
    • Development of a Highly α-Regioselective Metal-Mediated Allylation Reaction in Aqueous Media: New Mechanistic Proposal for the Origin of α-Homoallylic Alcohols
    • (c) Tan, K. T.; Chng, S. S.; Cheng, H. S.; Loh, T. P. Development of a Highly α-Regioselective Metal-Mediated Allylation Reaction in Aqueous Media: New Mechanistic Proposal for the Origin of α-Homoallylic Alcohols. J. Am. Chem. Soc. 2003, 125, 2958-2963;
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 2958-2963
    • Tan, K.T.1    Chng, S.S.2    Cheng, H.S.3    Loh, T.P.4
  • 5
    • 24044470646 scopus 로고    scopus 로고
    • Organic Reactions in Aqueous Media with a Focus on Carbon-Carbon Bond Formations: A Decade Update
    • (a) Li, C. J. Organic Reactions in Aqueous Media with a Focus on Carbon-Carbon Bond Formations: A Decade Update. Chem. Rev. 2005, 105, 3095-3165;
    • (2005) Chem. Rev , vol.105 , pp. 3095-3165
    • Li, C.J.1
  • 7
    • 0036736355 scopus 로고    scopus 로고
    • Origins, Current Status, and Future Challenges of Green Chemistry
    • Anastas, P. T.; Kirchhoff, M. M. Origins, Current Status, and Future Challenges of Green Chemistry. Acc. Chem. Res. 2002, 35, 686-694.
    • (2002) Acc. Chem. Res , vol.35 , pp. 686-694
    • Anastas, P.T.1    Kirchhoff, M.M.2
  • 8
    • 33845377368 scopus 로고
    • Allylzinc reagents additions in aqueous media
    • (a) Petrier, C.; Luche, J. L. Allylzinc reagents additions in aqueous media. J. Org. Chem. 1985, 50, 910-912;
    • (1985) J. Org. Chem , vol.50 , pp. 910-912
    • Petrier, C.1    Luche, J.L.2
  • 9
    • 0001424632 scopus 로고    scopus 로고
    • Study of the Allylation of Aldehydes with Allyl Halides in Cosolvent/Water(Salt)/Zn and in Cosolvent/Water(Salt)/Zn/Haloorganotin Media
    • (b) Marton, D.; Stivanello, D.; Tagliavini, G. Study of the Allylation of Aldehydes with Allyl Halides in Cosolvent/Water(Salt)/Zn and in Cosolvent/Water(Salt)/Zn/Haloorganotin Media. J. Org. Chem. 1996, 61, 2731-2737;
    • (1996) J. Org. Chem , vol.61 , pp. 2731-2737
    • Marton, D.1    Stivanello, D.2    Tagliavini, G.3
  • 10
    • 0242467642 scopus 로고    scopus 로고
    • Indium and zinc-mediated allylation of difluoroacetyltrialkylsilanes in aqueous media
    • (c) Chung, W.; Higashiya, S.; Oba, Y.; Welch, J. Indium and zinc-mediated allylation of difluoroacetyltrialkylsilanes in aqueous media. Tetrahedron 2003, 59, 10031-10036.
    • (2003) Tetrahedron , vol.59 , pp. 10031-10036
    • Chung, W.1    Higashiya, S.2    Oba, Y.3    Welch, J.4
  • 11
    • 0034670519 scopus 로고    scopus 로고
    • Organometallic Reactions in Aqueous Media. Indium and Zinc-Mediated Allylation of Sulfonimines
    • (d) Lu, W. S.; Chan, T. H. Organometallic Reactions in Aqueous Media. Indium and Zinc-Mediated Allylation of Sulfonimines. J. Org. Chem. 2000, 65, 8589-8594.
    • (2000) J. Org. Chem , vol.65 , pp. 8589-8594
    • Lu, W.S.1    Chan, T.H.2
  • 12
    • 0000698226 scopus 로고
    • Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminum
    • (a) Nokami, J.; Otera, J.; Sudo, T.; Okawara, R. Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminum. Organometallics 1983, 2, 191-193;
    • (1983) Organometallics , vol.2 , pp. 191-193
    • Nokami, J.1    Otera, J.2    Sudo, T.3    Okawara, R.4
  • 13
    • 37049078348 scopus 로고
    • Tin-promoted stereocontrolled intramolecular allylation of carbonyl-compounds - a facile and stereoselective method for ring construction
    • (b) Zhou, J. Y.; Chen, Z. G.; Wu, S. H. Tin-promoted stereocontrolled intramolecular allylation of carbonyl-compounds - a facile and stereoselective method for ring construction. Chem. Commun. 1994, 2783-2784.
    • (1994) Chem. Commun , pp. 2783-2784
    • Zhou, J.Y.1    Chen, Z.G.2    Wu, S.H.3
  • 14
    • 0028430856 scopus 로고
    • Ru-Lemieux-Award-Lecture - Organometallic-type Reactions in Aqueous-Media - A New Challenge in Organic-Synthesis
    • (a) Chan, T. H.; Li, C. J.; Lee, M. C.; Wei, Z. Y. 1993 Ru-Lemieux-Award-Lecture - Organometallic-type Reactions in Aqueous-Media - A New Challenge in Organic-Synthesis. Can. J. Chem. 1994, 72, 1181-1192;
    • (1993) Can. J. Chem , vol.1994 , Issue.72 , pp. 1181-1192
    • Chan, T.H.1    Li, C.J.2    Lee, M.C.3    Wei, Z.Y.4
  • 15
    • 0029933487 scopus 로고    scopus 로고
    • Addition of Allylindium Reagents to Aldehydes Substituted at Cα or Cβ with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems
    • (b) Paquette, L. A.; Mitzel, T. M. Addition of Allylindium Reagents to Aldehydes Substituted at Cα or Cβ with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems. J. Am. Chem. Soc. 1996, 118, 1931-1937;
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 1931-1937
    • Paquette, L.A.1    Mitzel, T.M.2
  • 16
    • 0001310676 scopus 로고    scopus 로고
    • Indium-Mediated Organometallic Reactions in Aqueous Media: The Nature of the Allylindium Intermediate
    • c) Chan, Y. H.; Yang, Y. J. Indium-Mediated Organometallic Reactions in Aqueous Media: The Nature of the Allylindium Intermediate. J. Am. Chem. Soc. 1999, 121, 3228-3229.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 3228-3229
    • Chan, Y.H.1    Yang, Y.J.2
  • 17
    • 0001470051 scopus 로고    scopus 로고
    • Manganese-Mediated Carbon-Carbon Bond Formation in Aqueous Media: Chemoselective Allylation and Pinacol Coupling of Aryl Aldehydes
    • Li, C. J.; Meng, Y.; Yi, X. H. Manganese-Mediated Carbon-Carbon Bond Formation in Aqueous Media: Chemoselective Allylation and Pinacol Coupling of Aryl Aldehydes. J. Org. Chem. 1998, 63, 7498-7504.
    • (1998) J. Org. Chem , vol.63 , pp. 7498-7504
    • Li, C.J.1    Meng, Y.2    Yi, X.H.3
  • 18
    • 0042158744 scopus 로고    scopus 로고
    • Carbon-carbon bond formation using bismuth in a water medium
    • (a) Miyamoto, H.; Daikawa, N.; Tanaka, K. Carbon-carbon bond formation using bismuth in a water medium. Tetrahedron Lett. 2003, 44, 6963-6964;
    • (2003) Tetrahedron Lett , vol.44 , pp. 6963-6964
    • Miyamoto, H.1    Daikawa, N.2    Tanaka, K.3
  • 19
    • 2342525330 scopus 로고    scopus 로고
    • Iron-mediated allylation of aryl aldehydes in aqueous media
    • (b) Chan, T. C.; Lau, C. P.; Chan, T. H. Iron-mediated allylation of aryl aldehydes in aqueous media. Tetrahedron Lett. 2004, 45, 4189-4191.
    • (2004) Tetrahedron Lett , vol.45 , pp. 4189-4191
    • Chan, T.C.1    Lau, C.P.2    Chan, T.H.3
  • 20
    • 0000595897 scopus 로고
    • Carbon-carbon bond formation in aqueous ethanol: Diastereoselective transformation of unprotected carbohydrates to higher carbon sugars using allyl bromide and tin metal
    • Schimd, W.; Whitesides, G. M. Carbon-carbon bond formation in aqueous ethanol: diastereoselective transformation of unprotected carbohydrates to higher carbon sugars using allyl bromide and tin metal. J. Am. Chem. Soc. 1991, 113, 6674-6675.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 6674-6675
    • Schimd, W.1    Whitesides, G.M.2
  • 21
    • 0000276890 scopus 로고    scopus 로고
    • Allylation of Carbonyl Compounds Bearing a Hydroxyl Group by Tetraallyltin: Highly Stereoselective Allylation in a Chelation-Controlled Manner
    • Yasuda, M.; Fujibayashi, T.; Baba, A. Allylation of Carbonyl Compounds Bearing a Hydroxyl Group by Tetraallyltin: Highly Stereoselective Allylation in a Chelation-Controlled Manner. J. Org. Chem. 1998, 63, 6401-6404.
    • (1998) J. Org. Chem , vol.63 , pp. 6401-6404
    • Yasuda, M.1    Fujibayashi, T.2    Baba, A.3
  • 22
    • 0037118363 scopus 로고    scopus 로고
    • Application of Tin and Nanometer Tin in Allylation of Carbonyl Compounds in Tap Water
    • Wang, Z.; Zha, Z.; Zhou, C. Application of Tin and Nanometer Tin in Allylation of Carbonyl Compounds in Tap Water Org. Lett. 2002, 4, 1683-1685.
    • (2002) Org. Lett , vol.4 , pp. 1683-1685
    • Wang, Z.1    Zha, Z.2    Zhou, C.3
  • 23
    • 13644266895 scopus 로고    scopus 로고
    • Barbier-type reaction mediated with tin nano-particles in water
    • Zha, Z.; Qiao, S. Q.; Jiang, J.; Wang, Y.; Miao, Q.; Wang, Z. Barbier-type reaction mediated with tin nano-particles in water. Tetrahedron 2005, 61, 2521-2527.
    • (2005) Tetrahedron , vol.61 , pp. 2521-2527
    • Zha, Z.1    Qiao, S.Q.2    Jiang, J.3    Wang, Y.4    Miao, Q.5    Wang, Z.6
  • 24
    • 19544365434 scopus 로고    scopus 로고
    • Zha, Z.; Hui, A.; Zhou, Y.; Miao, Q.; Wang, Z.; Zhang, H. A Recyclable Electrochemical Allylation in Water. Org. Lett. 2005, 7, 1903-1905.
    • Zha, Z.; Hui, A.; Zhou, Y.; Miao, Q.; Wang, Z.; Zhang, H. A Recyclable Electrochemical Allylation in Water. Org. Lett. 2005, 7, 1903-1905.
  • 25
    • 0000888349 scopus 로고
    • Palladium-catalyzed carbonyl allylation by allylic alcohols with stannous chloride
    • (a) Takahara, J. P.; Masuyama, Y.; Kumsu, Y. Palladium-catalyzed carbonyl allylation by allylic alcohols with stannous chloride. J. Am. Chem. Soc. 1992, 114, 2577-2586;
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 2577-2586
    • Takahara, J.P.1    Masuyama, Y.2    Kumsu, Y.3
  • 26
    • 0000160298 scopus 로고    scopus 로고
    • Reformatsky Reaction in Water: Evidence for a Radical Chain Process
    • b) Bieber, L. W.; Malvestiti, I.; Storch, E. C. Reformatsky Reaction in Water: Evidence for a Radical Chain Process. J. Org. Chem. 1997, 62, 9061-9064.
    • (1997) J. Org. Chem , vol.62 , pp. 9061-9064
    • Bieber, L.W.1    Malvestiti, I.2    Storch, E.C.3
  • 28
    • 0000546977 scopus 로고
    • Bismuth(III) Chloride Aluminum-promoted Allylation of Aldehydes to Homoallylic Alcohols in Aqueous Solvent
    • Wada, M.; Ohki, H.; Akiba, K. -Y. Bismuth(III) Chloride Aluminum-promoted Allylation of Aldehydes to Homoallylic Alcohols in Aqueous Solvent. Bull. Chem. Soc. Jpn. 1990, 1738-1747.
    • (1990) Bull. Chem. Soc. Jpn , pp. 1738-1747
    • Wada, M.1    Ohki, H.2    Akiba, K.-Y.3
  • 29
    • 33847085986 scopus 로고    scopus 로고
    • Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursors. J. Am. Chem. Soc. 1980, 102, 7107-7109;
    • (a) Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. Erythro-selective addition of crotyltrialkyltins to aldehydes regardless of the geometry of the crotyl unit. Stereoselection independent of the stereochemistry of precursors. J. Am. Chem. Soc. 1980, 102, 7107-7109;
  • 30
    • 13644266895 scopus 로고    scopus 로고
    • Barbier-type reaction mediated with tin nano-particles in water
    • (b) Zha, Z.; Quiao, S. Q.; Jiang, J.; Wang, Y.; Miao, Q.; Wang, Z. Barbier-type reaction mediated with tin nano-particles in water. Tetrahedron 2005, 61, 2521-2527.
    • (2005) Tetrahedron , vol.61 , pp. 2521-2527
    • Zha, Z.1    Quiao, S.Q.2    Jiang, J.3    Wang, Y.4    Miao, Q.5    Wang, Z.6
  • 31
    • 0039874886 scopus 로고    scopus 로고
    • Comparative diastereoselectivity analysis of crotylindium and 3-bromoallylindium additions to α-oxy aldehydes in aqueous and nonaqueous solvent systems
    • (a) Paquette, L.A.; Mitzel, T.M. Comparative diastereoselectivity analysis of crotylindium and 3-bromoallylindium additions to α-oxy aldehydes in aqueous and nonaqueous solvent systems, J. Org. Chem. 1996, 61, 8799-8804;
    • (1996) J. Org. Chem , vol.61 , pp. 8799-8804
    • Paquette, L.A.1    Mitzel, T.M.2
  • 32
    • 0035906473 scopus 로고    scopus 로고
    • Indium-mediated organometallic reactions in aqueous media. Stereoselectivity in crotylation of sulfonimines bearing a proximal chelating group
    • (b) Chung, W., Chan, T. H. Indium-mediated organometallic reactions in aqueous media. Stereoselectivity in crotylation of sulfonimines bearing a proximal chelating group. J. Org. Chem. 2001, 66, 3467-3473.
    • (2001) J. Org. Chem , vol.66 , pp. 3467-3473
    • Chung, W.1    Chan, T.H.2
  • 33
    • 0000732942 scopus 로고
    • Hydrated sigma-bonded organometallic cations in organic-synthesis. 1. allyl-stannation, crotyl-stannation, 1-methylallyl-stannation, cyclohex-2-enyl-stannation, and cinnamyl-stannation of carbonyl-compounds in water
    • Furlani, D.; Marton, D.; Tagliavini, G.; Zordan, M. Hydrated sigma-bonded organometallic cations in organic-synthesis. 1. allyl-stannation, crotyl-stannation, 1-methylallyl-stannation, cyclohex-2-enyl-stannation, and cinnamyl-stannation of carbonyl-compounds in water. J. Organomet. Chem. 1988, 341, 345-356.
    • (1988) J. Organomet. Chem , vol.341 , pp. 345-356
    • Furlani, D.1    Marton, D.2    Tagliavini, G.3    Zordan, M.4
  • 34
    • 1642578075 scopus 로고    scopus 로고
    • 2O and Surface Diagnostics
    • 2O and Surface Diagnostics. Organometallics 2004, 23, 67-71.
    • (2004) Organometallics , vol.23 , pp. 67-71
    • Sinha, P.1    Roy, S.2
  • 35
    • 0001134456 scopus 로고    scopus 로고
    • Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization
    • Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Oxonia-Cope Rearrangement and Side-Chain Exchange in the Prins Cyclization. Org. Lett. 2002, 4, 577-580.
    • (2002) Org. Lett , vol.4 , pp. 577-580
    • Crosby, S.R.1    Harding, J.R.2    King, C.D.3    Parker, G.D.4    Willis, C.L.5
  • 36
    • 33750041945 scopus 로고    scopus 로고
    • Racemization in Prins Cyclization Reactions
    • Jasti, R.; Rychnovsky, S. D.; Racemization in Prins Cyclization Reactions. J. Am. Chem. Soc. 2006, 128, 13640-13648.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 13640-13648
    • Jasti, R.1    Rychnovsky, S.D.2
  • 38
    • 0018468081 scopus 로고
    • Electrochemical reduction of allyl halides in nonaqueous solvents - a reinvestigation
    • Bard, A.J; Merz, A. Electrochemical reduction of allyl halides in nonaqueous solvents - a reinvestigation. J. Am. Chem. Soc. 1979, 101, 2959-2965.
    • (1979) J. Am. Chem. Soc , vol.101 , pp. 2959-2965
    • Bard, A.J.1    Merz, A.2
  • 39
    • 0000745524 scopus 로고
    • Kinetics of nitroxide radical trapping. 1. Solvent effects
    • (a) Beckwith, A. L. J.; Bowry, V. W.; Ingold, K. U. Kinetics of nitroxide radical trapping. 1. Solvent effects. J. Am. Chem. Soc. 1992, 114, 4983-4992;
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 4983-4992
    • Beckwith, A.L.J.1    Bowry, V.W.2    Ingold, K.U.3
  • 40
    • 0000745523 scopus 로고
    • Kinetics of nitroxide radical trapping. 2. Structural effects
    • b) Bowry, V. W.; Ingold, K. U. Kinetics of nitroxide radical trapping. 2. Structural effects. J. Am. Chem. Soc. 1992, 114, 4992-4996.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 4992-4996
    • Bowry, V.W.1    Ingold, K.U.2
  • 41
    • 0000544750 scopus 로고
    • 3-Promoted Addition of Allylic Stannanes to Aldehydes
    • 3-Promoted Addition of Allylic Stannanes to Aldehydes. J. Org. Chem. 1995, 60, 1920-1921.
    • (1995) J. Org. Chem , vol.60 , pp. 1920-1921
    • Marshall, J.A.1    Hinkle, K.W.2
  • 42
    • 0037594866 scopus 로고    scopus 로고
    • Organometallic Reactions in Aqueous Media. The Nature of the Organotin Intermediate in the Tin-Mediated Allylation of Carbonyl Compounds
    • Chan, T. H.; Yang, Y.; Li, C. J. Organometallic Reactions in Aqueous Media. The Nature of the Organotin Intermediate in the Tin-Mediated Allylation of Carbonyl Compounds. J. Org. Chem. 1999, 64, 4452-4455.
    • (1999) J. Org. Chem , vol.64 , pp. 4452-4455
    • Chan, T.H.1    Yang, Y.2    Li, C.J.3
  • 43
    • 16244384662 scopus 로고    scopus 로고
    • Theoretical study of Intrinsic reactivities of various allylmetals toward carbonyl and water
    • Chung, L. W.; Chan, T. H.; Wu, Y.D. Theoretical study of Intrinsic reactivities of various allylmetals toward carbonyl and water. Organometallics 2005, 24, 1598-1607.
    • (2005) Organometallics , vol.24 , pp. 1598-1607
    • Chung, L.W.1    Chan, T.H.2    Wu, Y.D.3
  • 44
  • 45
    • 2542423081 scopus 로고    scopus 로고
    • Synthetic aspects of tetraorganotins and organotin(IV) halides
    • Thoonen, S. H. L.; Deelman, B. J.; Koten, G. Synthetic aspects of tetraorganotins and organotin(IV) halides. J. Organomet. Chem. 2004, 689, 2145-2157.
    • (2004) J. Organomet. Chem , vol.689 , pp. 2145-2157
    • Thoonen, S.H.L.1    Deelman, B.J.2    Koten, G.3
  • 47
    • 33846325209 scopus 로고
    • NMR-spectra and structures of organotin compounds
    • Petrosyan, V.S. NMR-spectra and structures of organotin compounds Prog. NMR Spectrosc. 1977, 11, 115-148.
    • (1977) Prog. NMR Spectrosc , vol.11 , pp. 115-148
    • Petrosyan, V.S.1


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