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Volumn 42, Issue 6, 2009, Pages 756-768

Synthesis of aminoboronic acids and their applications in bifunctional catalysis

Author keywords

[No Author keywords available]

Indexed keywords

8 QUINOLINEBORONIC ACID; 8-QUINOLINEBORONIC ACID; AMINO ACID; BORONIC ACID DERIVATIVE; CHLOROHYDRIN DERIVATIVE; HALOGEN; LITHIUM; QUINOLINE DERIVATIVE;

EID: 67649231343     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800262v     Document Type: Article
Times cited : (130)

References (47)
  • 3
    • 0001036387 scopus 로고
    • Organoboron compounds. XI. 8- Quinolineboronic acid, its preparation and influence on reaction of chlorohydrins
    • Letsinger, R. L.; Dandegaonker, S. H. Organoboron compounds. XI. 8- Quinolineboronic acid, its preparation and influence on reaction of chlorohydrins. J. Am. Chem. Soc.1959, 81, 498-501.
    • (1959) J. Am. Chem. Soc , vol.81 , pp. 498-501
    • Letsinger, R.L.1    Dandegaonker, S.H.2
  • 4
    • 33747891699 scopus 로고
    • Organoboron compounds. XVII. Chemistry of a compound with neighbouring borono, ethynyl, and amine functional groups
    • Letsinger, R. L.; Wysocki, A. J. Organoboron compounds. XVII. Chemistry of a compound with neighbouring borono, ethynyl, and amine functional groups. J. Org. Chem.1963, 28, 3199-3202.
    • (1963) J. Org. Chem , vol.28 , pp. 3199-3202
    • Letsinger, R.L.1    Wysocki, A.J.2
  • 6
    • 33845555248 scopus 로고
    • Directed lithiation of aromatic tertiary amides: An evolving synthetic methodology for polysubstituted aromatics
    • Beak, P.; Snieckus, V. Directed lithiation of aromatic tertiary amides: An evolving synthetic methodology for polysubstituted aromatics. Acc. Chem. Res.1982, 15, 306-312.
    • (1982) Acc. Chem. Res , vol.15 , pp. 306-312
    • Beak, P.1    Snieckus, V.2
  • 7
    • 0002722516 scopus 로고
    • Arylboronic acids with intramolecular B-N interaction: Convenient synthesis through ortho-lithiation of substituted benzylamines
    • Lauer, M.; Wulff, G. Arylboronic acids with intramolecular B-N interaction: Convenient synthesis through ortho-lithiation of substituted benzylamines. J. Organomet. Chem.1983, 256, 1-9.
    • (1983) J. Organomet. Chem , vol.256 , pp. 1-9
    • Lauer, M.1    Wulff, G.2
  • 8
    • 0041387372 scopus 로고    scopus 로고
    • Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 1-N,N-Dimethylamino-8-borononaphthalene derivatives
    • Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 1-N,N-Dimethylamino-8-borononaphthalene derivatives. J. Organomet. Chem.2003, 680, 257-262.
    • (2003) J. Organomet. Chem , vol.680 , pp. 257-262
    • Giles, R.L.1    Howard, J.A.K.2    Patrick, L.G.F.3    Probert, M.R.4    Smith, G.E.5    Whiting, A.6
  • 9
    • 26444588068 scopus 로고    scopus 로고
    • Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 2-N,N- Diisopropylaminobenzylboronate derivatives
    • Coghlan, S. W.; Giles, R. L.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Smith, G. E.; Whiting, A. Synthesis and structure of potential Lewis acid-Lewis base bifunctional catalysts: 2-N,N- Diisopropylaminobenzylboronate derivatives. J. Organomet. Chem.2005, 690, 4784-4793.
    • (2005) J. Organomet. Chem , vol.690 , pp. 4784-4793
    • Coghlan, S.W.1    Giles, R.L.2    Howard, J.A.K.3    Patrick, L.G.F.4    Probert, M.R.5    Smith, G.E.6    Whiting, A.7
  • 10
    • 20644467160 scopus 로고
    • Unsymmetrically disubstituted ferrocenes. Part IV. The synthesis and reactivity of 2-(N,N- dimethylaminomethyl)ferroceneboronic acid
    • Marr, G.; Moore, R. E.; Rockett, B. W. Unsymmetrically disubstituted ferrocenes. Part IV. The synthesis and reactivity of 2-(N,N- dimethylaminomethyl)ferroceneboronic acid. J. Chem. Soc. C1968, 24-27.
    • (1968) J. Chem. Soc. C , pp. 24-27
    • Marr, G.1    Moore, R.E.2    Rockett, B.W.3
  • 11
    • 0033395841 scopus 로고    scopus 로고
    • Chiral ferrocene derivatives containing a 2,2'-bridged binaphthyl moiety
    • Widhalm, M.; Nettekoven, U.; Mereiter, K. Chiral ferrocene derivatives containing a 2,2'-bridged binaphthyl moiety. Tetrahedron: Asymmetry1999, 10, 4369-4391.
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 4369-4391
    • Widhalm, M.1    Nettekoven, U.2    Mereiter, K.3
  • 12
    • 0343435902 scopus 로고
    • Stereoselective syntheses. VI. Correlation of central and planar chirality in ferrocene derivatives
    • Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. Stereoselective syntheses. VI. Correlation of central and planar chirality in ferrocene derivatives. J. Am. Chem. Soc.1970, 92, 5389-5393.
    • (1970) J. Am. Chem. Soc , vol.92 , pp. 5389-5393
    • Marquarding, D.1    Klusacek, H.2    Gokel, G.3    Hoffmann, P.4    Ugi, I.5
  • 13
    • 33947087421 scopus 로고
    • Stereoselective synthesis. VIII. Absolute configuration of a 1,2-disubstituted ferrocene derivative with planar and central elements of chirality and the mechanism of the optically active R-ferrocenyl tertiary amines
    • Battelle, L. F.; Bau, R.; Gokel, G. W.; Oyakawa, R. T.; Ugi, I. Stereoselective synthesis. VIII. Absolute configuration of a 1,2-disubstituted ferrocene derivative with planar and central elements of chirality and the mechanism of the optically active R-ferrocenyl tertiary amines. J. Am. Chem. Soc.1973, 95, 482-486.
    • (1973) J. Am. Chem. Soc , vol.95 , pp. 482-486
    • Battelle, L.F.1    Bau, R.2    Gokel, G.W.3    Oyakawa, R.T.4    Ugi, I.5
  • 14
    • 33748231903 scopus 로고
    • Asymmetric synthesis and highly diastereoselective ortho-lithiation of ferrocenyl sulfoxides. Application to the synthesis of ferrocenyl derivatives with planar chirality
    • Rebière, F.; Riant, O.; Ricard, L.; Kagan, H. B. Asymmetric synthesis and highly diastereoselective ortho-lithiation of ferrocenyl sulfoxides. Application to the synthesis of ferrocenyl derivatives with planar chirality. Angew. Chem., Int. Ed. Engl.1993, 32, 568-570.
    • (1993) Angew. Chem., Int. Ed. Engl , vol.32 , pp. 568-570
    • Rebière, F.1    Riant, O.2    Ricard, L.3    Kagan, H.B.4
  • 15
    • 0000996454 scopus 로고
    • A general asymmetric synthesis of ferrocenes with planar chirality
    • Riant, O.; Samuel, O.; Kagan, H. B. A general asymmetric synthesis of ferrocenes with planar chirality. J. Am. Chem. Soc.1993, 115, 5835-5836.
    • (1993) J. Am. Chem. Soc , vol.115 , pp. 5835-5836
    • Riant, O.1    Samuel, O.2    Kagan, H.B.3
  • 16
    • 85049751006 scopus 로고
    • Asymmetric synthesis and highly diastereoselective ortho-lithiation of oxazolinylferrocenes
    • Nishibayashi, Y.; Uemura, S. Asymmetric synthesis and highly diastereoselective ortho-lithiation of oxazolinylferrocenes. Synlett1995, 79- 80.
    • (1995) Synlett , pp. 79-80
    • Nishibayashi, Y.1    Uemura, S.2
  • 17
    • 33751157112 scopus 로고
    • Highly diastereoselective ortholithiations of chiral oxazoline-substituted ferrocenes
    • Sammakia, T.; Latham, H. A.; Schaad, D. R. Highly diastereoselective ortholithiations of chiral oxazoline-substituted ferrocenes. J. Org. Chem.1995, 60, 10- 11.
    • (1995) J. Org. Chem , vol.60 , pp. 10-11
    • Sammakia, T.1    Latham, H.A.2    Schaad, D.R.3
  • 18
    • 85049755071 scopus 로고
    • Synthesis of 2-[2-(diphenylphosphino)ferrocenyl]oxazoline ligands
    • Richards, C. J.; Damalidis, T.; Hibbs, D. E.; Hursthouse, M. B. Synthesis of 2-[2-(diphenylphosphino)ferrocenyl]oxazoline ligands. Synlett1995, 74-75.
    • (1995) Synlett , pp. 74-75
    • Richards, C.J.1    Damalidis, T.2    Hibbs, D.E.3    Hursthouse, M.B.4
  • 19
    • 0142227197 scopus 로고    scopus 로고
    • Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers
    • Anderson, J. C.; Blake, A. J.; Arnall-Culliford, J. C. Synthesis of planar chiral ferrocenyl 1,3-diamines and 1,3-amino ethers. Org. Biomol. Chem.2003, 1, 3586- 3591.
    • (2003) Org. Biomol. Chem , vol.1 , pp. 3586-3591
    • Anderson, J.C.1    Blake, A.J.2    Arnall-Culliford, J.C.3
  • 20
    • 2942588905 scopus 로고    scopus 로고
    • Mechanically induced expeditious and selective preparation of disubstituted pyridine/pyrimidine ferrocenyl complexes
    • Braga, D.; D'Addario, D.; Polito, M.; Grepioni, F. Mechanically induced expeditious and selective preparation of disubstituted pyridine/pyrimidine ferrocenyl complexes. Organometallics2004, 23, 2810-2812.
    • (2004) Organometallics , vol.23 , pp. 2810-2812
    • Braga, D.1    D'Addario, D.2    Polito, M.3    Grepioni, F.4
  • 21
    • 0000527506 scopus 로고    scopus 로고
    • Direct and highly enantioselective synthesis of ferrocenes with planar chirality by (-)-sparteine-mediated lithiation
    • Tsukazaki, M.; Tinkl, M.; Roglans, A.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. Direct and highly enantioselective synthesis of ferrocenes with planar chirality by (-)-sparteine-mediated lithiation. J. Am. Chem. Soc.1996, 118, 685-686.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 685-686
    • Tsukazaki, M.1    Tinkl, M.2    Roglans, A.3    Chapell, B.J.4    Taylor, N.J.5    Snieckus, V.6
  • 22
    • 34248524652 scopus 로고    scopus 로고
    • Synthesis and structure of planar chiral, bifunctional amino-boronic acid ferrocene derivatives
    • Batsanov, A. S.; Herault, D.; Howard, J. A. K.; Patrick, L. G. F.; Probert, M. R.; Whiting, A. Synthesis and structure of planar chiral, bifunctional amino-boronic acid ferrocene derivatives. Organometallics2007, 26, 2414-2419.
    • (2007) Organometallics , vol.26 , pp. 2414-2419
    • Batsanov, A.S.1    Herault, D.2    Howard, J.A.K.3    Patrick, L.G.F.4    Probert, M.R.5    Whiting, A.6
  • 23
    • 41949131110 scopus 로고    scopus 로고
    • Asymmetric direct amide synthesis via kinetic amine resolution: A chiral bifunctional amino-boronic acid catalyzed reaction between a racemic amine and achiral carboxylic acid
    • Arnold, K.; Davies, B.; Hérault, D.; Whiting, A. Asymmetric direct amide synthesis via kinetic amine resolution: A chiral bifunctional amino-boronic acid catalyzed reaction between a racemic amine and achiral carboxylic acid. Angew. Chem., Int. Ed.2008, 47, 2673-2676.
    • (2008) Angew. Chem., Int. Ed , vol.47 , pp. 2673-2676
    • Arnold, K.1    Davies, B.2    Hérault, D.3    Whiting, A.4
  • 24
    • 61349173922 scopus 로고    scopus 로고
    • Aminoferrocene lithiation by boron trifluoride activation
    • Metallinos, C.; Zaifman, J.; Dodge, L. Aminoferrocene lithiation by boron trifluoride activation. Org. Lett.2008, 10, 3527-3530.
    • (2008) Org. Lett , vol.10 , pp. 3527-3530
    • Metallinos, C.1    Zaifman, J.2    Dodge, L.3
  • 25
    • 0000793111 scopus 로고
    • Synthesis and properties of pinanediol R-amido boronic esters
    • Matteson, D. S.; Jesthi, P. K.; Sadhu, K. M. Synthesis and properties of pinanediol R-amido boronic esters. Organometallics1984, 3, 1284-1288.
    • (1984) Organometallics , vol.3 , pp. 1284-1288
    • Matteson, D.S.1    Jesthi, P.K.2    Sadhu, K.M.3
  • 26
    • 0025234721 scopus 로고    scopus 로고
    • Bachovchin, W. W.; Plaut, A. G.; Flentke, G. R.; Lynch, M.; Kettner, C. A. Inhibition of IgA1 proteinases from Neisseria gonorrhoeaeand Hemophilius influenzaeby peptide prolyl boronic acid. J. Biol. Chem.1990, 265, 3738-3743.
    • Bachovchin, W. W.; Plaut, A. G.; Flentke, G. R.; Lynch, M.; Kettner, C. A. Inhibition of IgA1 proteinases from Neisseria gonorrhoeaeand Hemophilius influenzaeby peptide prolyl boronic acid. J. Biol. Chem.1990, 265, 3738-3743.
  • 27
    • 33845185331 scopus 로고    scopus 로고
    • Matteson, D. S. R-Halo boronic esterssIntermediates for stereodirected synthesis. Chem. Rev.1989, 89, 1535-1551. (b) Matteson, D. S. Boronic esters in stereodirected synthesis. Tetrahedron1989, 45, 1859-1885. (c) Matteson, D. S. Functional group compatibilities in boronic ester chemistry. J. Organomet. Chem.1999, 581, 51-65. Also, see (d) Dembitsky, V. M.; Srebnik, M. Synthesis and biological activity of R-aminoboronic acids, amine-carboxyboranes and their derivatives. Tetrahedron2003, 59, 579-593.
    • Matteson, D. S. R-Halo boronic esterssIntermediates for stereodirected synthesis. Chem. Rev.1989, 89, 1535-1551. (b) Matteson, D. S. Boronic esters in stereodirected synthesis. Tetrahedron1989, 45, 1859-1885. (c) Matteson, D. S. Functional group compatibilities in boronic ester chemistry. J. Organomet. Chem.1999, 581, 51-65. Also, see (d) Dembitsky, V. M.; Srebnik, M. Synthesis and biological activity of R-aminoboronic acids, amine-carboxyboranes and their derivatives. Tetrahedron2003, 59, 579-593.
  • 28
    • 0000920450 scopus 로고
    • Complex-induced proximity effectssEnantioselective synthesis based on asymmetric deprotonation of N-Bocpyrrolidines
    • Beak, P.; Kerrick, S. I.; Wu, S. D.; Chu, J. X. Complex-induced proximity effectssEnantioselective synthesis based on asymmetric deprotonation of N-Bocpyrrolidines. J. Am. Chem. Soc.1994, 116, 3231-3239.
    • (1994) J. Am. Chem. Soc , vol.116 , pp. 3231-3239
    • Beak, P.1    Kerrick, S.I.2    Wu, S.D.3    Chu, J.X.4
  • 29
    • 34547630741 scopus 로고    scopus 로고
    • A (-)-sparteine directed highly enantioselective synthesis of boroproline. Solid and solution state structure and properties
    • Batsanov, A. S.; Grosjean, C.; Schütz, T.; Whiting, A. A (-)-sparteine directed highly enantioselective synthesis of boroproline. Solid and solution state structure and properties. J. Org. Chem.2007, 72, 6276-6279.
    • (2007) J. Org. Chem , vol.72 , pp. 6276-6279
    • Batsanov, A.S.1    Grosjean, C.2    Schütz, T.3    Whiting, A.4
  • 30
    • 50249116718 scopus 로고    scopus 로고
    • The first example of enamine-Lewis acid cooperative bifunctional catalysis: Application to the asymmetric aldol reaction
    • Arnold, K.; Batsanov, A. S.; Davies, B.; Grosjean, C.; Schütz, T.; Whiting, A.; Zawatzky, K. The first example of enamine-Lewis acid cooperative bifunctional catalysis: Application to the asymmetric aldol reaction. Chem. Commun.2008, 3879-3881.
    • (2008) Chem. Commun , pp. 3879-3881
    • Arnold, K.1    Batsanov, A.S.2    Davies, B.3    Grosjean, C.4    Schütz, T.5    Whiting, A.6    Zawatzky, K.7
  • 31
    • 0001275870 scopus 로고    scopus 로고
    • Matteson, D.; Sadhu, K. M. Boronic ester homologation with 99% chiral selectivity and its use in syntheses of the insect pheromones (3S,4S)-4-methyl-3-heptanol and exo-brevicomin. J. Am. Chem. Soc.1983, 105, 2077-2078.
    • Matteson, D.; Sadhu, K. M. Boronic ester homologation with 99% chiral selectivity and its use in syntheses of the insect pheromones (3S,4S)-4-methyl-3-heptanol and exo-brevicomin. J. Am. Chem. Soc.1983, 105, 2077-2078.
  • 32
    • 0033617155 scopus 로고    scopus 로고
    • New efficient method for the total synthesis of (S,S)- isodityrosine from natural amino acids
    • Jung, M. E.; Lazarova, T. I. New efficient method for the total synthesis of (S,S)- isodityrosine from natural amino acids. J. Org. Chem.1999, 64, 2976-2977.
    • (1999) J. Org. Chem , vol.64 , pp. 2976-2977
    • Jung, M.E.1    Lazarova, T.I.2
  • 33
    • 0030814396 scopus 로고    scopus 로고
    • Asymmetric synthesis of (R)- and (S)-2- pyrrolidinemethanesulfonic acid
    • Braghiroli, D.; Avallone, R.; Di Bella, M. Asymmetric synthesis of (R)- and (S)-2- pyrrolidinemethanesulfonic acid. Tetrahedron: Asymmetry1997, 8, 2209-2213.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2209-2213
    • Braghiroli, D.1    Avallone, R.2    Di Bella, M.3
  • 34
    • 0037030643 scopus 로고    scopus 로고
    • Endomorphin-1 analogues containing fi-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance
    • Cardillo, G.; Gentillucci, L.; Qasem, A.; Sgarzi, F.; Spampinato, S. Endomorphin-1 analogues containing fi-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance. J. Med. Chem.2002, 45, 2571-2578.
    • (2002) J. Med. Chem , vol.45 , pp. 2571-2578
    • Cardillo, G.1    Gentillucci, L.2    Qasem, A.3    Sgarzi, F.4    Spampinato, S.5
  • 35
    • 0038108990 scopus 로고    scopus 로고
    • Enzymecatalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP
    • Kurokawa, M.; Shindo, T.; Suzuki, M.; Nakajima, N.; Ishihara, K.; Sugai, T. Enzymecatalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP. Tetrahedron: Asymmetry2003, 14, 1323-1334.
    • (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1323-1334
    • Kurokawa, M.1    Shindo, T.2    Suzuki, M.3    Nakajima, N.4    Ishihara, K.5    Sugai, T.6
  • 36
    • 0042412181 scopus 로고
    • Organoboron compounds. XVI. Cooperative functional group effects in reactions of boronoarylbenzimidazoles
    • Letsinger, R. L.; MacLean, D. B. Organoboron compounds. XVI. Cooperative functional group effects in reactions of boronoarylbenzimidazoles. J. Am. Chem. Soc.1963, 85, 2230-2236.
    • (1963) J. Am. Chem. Soc , vol.85 , pp. 2230-2236
    • Letsinger, R.L.1    MacLean, D.B.2
  • 37
    • 0005095627 scopus 로고
    • Organoboron compounds. XX. Chemistry of some 1-naphthaleneboronic acids with substituents in the 8-position
    • Letsinger, R. L.; Smith, J. M.; Gilpin, J.; MacLean, D. B. Organoboron compounds. XX. Chemistry of some 1-naphthaleneboronic acids with substituents in the 8-position. J. Org. Chem.1965, 30, 807-812.
    • (1965) J. Org. Chem , vol.30 , pp. 807-812
    • Letsinger, R.L.1    Smith, J.M.2    Gilpin, J.3    MacLean, D.B.4
  • 38
    • 1542347971 scopus 로고    scopus 로고
    • Cation-cation interactions between uranyl cations in a polar open-framework uranyl periodate
    • Zhu, L.; Anslyn, E. V. Cation-cation interactions between uranyl cations in a polar open-framework uranyl periodate. J. Am. Chem. Soc.2004, 126, 2676-3677.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 2676-3677
    • Zhu, L.1    Anslyn, E.V.2
  • 39
    • 16244420077 scopus 로고    scopus 로고
    • Guidelines in implementing enantioselective indicator-displacement assays for R-hydroxycarboxylates and diols
    • Zhu, L.; Zhong, Z.; Anslyn, E. V. Guidelines in implementing enantioselective indicator-displacement assays for R-hydroxycarboxylates and diols. J. Am. Chem. Soc.2005, 127, 4260-4269.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 4260-4269
    • Zhu, L.1    Zhong, Z.2    Anslyn, E.V.3
  • 40
    • 31944449355 scopus 로고    scopus 로고
    • A structural investigation of the N-B interaction in an o-(N, N-dialkylaminomethyl)arylboronate system
    • Zhu, L.; Shabbir, H.; Gray, M.; Lynch, V. M.; Sorey, S.; Anslyn, E. V. A structural investigation of the N-B interaction in an o-(N, N-dialkylaminomethyl)arylboronate system. J. Am. Chem. Soc.2006, 128, 1222-1232.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 1222-1232
    • Zhu, L.1    Shabbir, H.2    Gray, M.3    Lynch, V.M.4    Sorey, S.5    Anslyn, E.V.6
  • 41
    • 0000078528 scopus 로고
    • Boronic acid catalyzed hydrolyses of salicylaldehyde imines
    • and references therein
    • Rao, G.; Philipp, M. Boronic acid catalyzed hydrolyses of salicylaldehyde imines. J. Org. Chem.1991, 56, 1505-1512, and references therein.
    • (1991) J. Org. Chem , vol.56 , pp. 1505-1512
    • Rao, G.1    Philipp, M.2
  • 42
    • 0345661260 scopus 로고
    • Organoboron compounds. XIV. Polyfunctional catalysis by 8-quinolineboronic acid
    • Letsinger, R. L.; Dandegaonker, S.; Vullo, W. J.; Morrison, J. D. Organoboron compounds. XIV. Polyfunctional catalysis by 8-quinolineboronic acid. J. Am. Chem. Soc.1963, 85, 2223-2227.
    • (1963) J. Am. Chem. Soc , vol.85 , pp. 2223-2227
    • Letsinger, R.L.1    Dandegaonker, S.2    Vullo, W.J.3    Morrison, J.D.4
  • 43
    • 2842598110 scopus 로고
    • Organoboron compounds. XV. Stereochemistry of the reaction of 8-quinolineboronic acid with chloroalcohols
    • Letsinger, R. L.; Morrison, J. D. Organoboron compounds. XV. Stereochemistry of the reaction of 8-quinolineboronic acid with chloroalcohols. J. Am. Chem. Soc.1963, 85, 2227-2230.
    • (1963) J. Am. Chem. Soc , vol.85 , pp. 2227-2230
    • Letsinger, R.L.1    Morrison, J.D.2
  • 44
    • 0042412181 scopus 로고
    • Organoboron compounds. XVI. Cooperative functional group effects in reactions of boronoarylbenzimidazoles
    • Letsinger, R. L.; MacLean, D. B. Organoboron compounds. XVI. Cooperative functional group effects in reactions of boronoarylbenzimidazoles. J. Am. Chem. Soc.1963, 85, 2230-2233.
    • (1963) J. Am. Chem. Soc , vol.85 , pp. 2230-2233
    • Letsinger, R.L.1    MacLean, D.B.2
  • 45
    • 33744790869 scopus 로고    scopus 로고
    • To catalyze or not to catalyze? Insight into direct amide bond formation from amines and carboxylic acids under thermal and catalyzed conditions
    • Arnold, K.; Davies, B.; Giles, R. L.; Grosjean, C.; Smith, G. E.; Whiting, A. To catalyze or not to catalyze? Insight into direct amide bond formation from amines and carboxylic acids under thermal and catalyzed conditions. Adv. Synth. Catal.2006, 348, 813-820.
    • (2006) Adv. Synth. Catal , vol.348 , pp. 813-820
    • Arnold, K.1    Davies, B.2    Giles, R.L.3    Grosjean, C.4    Smith, G.E.5    Whiting, A.6
  • 46
    • 37849029610 scopus 로고    scopus 로고
    • Synthesis, evaluation and application of novel bifunctional N,N-di- isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines
    • Arnold, K.; Batsanov, A. S.; Davies, B.; Whiting, A. Synthesis, evaluation and application of novel bifunctional N,N-di- isopropylbenzylamineboronic acid catalysts for direct amide formation between carboxylic acids and amines. Green Chem.2008, 10, 124-134.
    • (2008) Green Chem , vol.10 , pp. 124-134
    • Arnold, K.1    Batsanov, A.S.2    Davies, B.3    Whiting, A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.