메뉴 건너뛰기




Volumn 3, Issue 6, 2015, Pages 1221-1226

Waste minimized multistep preparation in flow of β-amino acids starting from α,β-unsaturated carboxylic acids

Author keywords

Amino acids; Cobalt boride; Multistep process; Waste minimization

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; CONSERVATION;

EID: 84930684196     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00185     Document Type: Article
Times cited : (17)

References (60)
  • 1
    • 0023676374 scopus 로고
    • Biosynthesis of Blasticidin S from l -α-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction
    • Prabhakaran, P. C.; Woo, N.-T.; Yorgey, P. S.; Gould, S. J. Biosynthesis of Blasticidin S from l -α-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction J. Am. Chem. Soc. 1988, 110, 5785-5791
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5785-5791
    • Prabhakaran, P.C.1    Woo, N.-T.2    Yorgey, P.S.3    Gould, S.J.4
  • 2
    • 0141764859 scopus 로고    scopus 로고
    • Identification and cloning of genes encoding viomycin biosynthesis from Streptomyces vinaceus and evidence for involvement of a rare oxygenase
    • Yin, X.; OHare, T.; Gould, S. J.; Zabriskie, T. M. Identification and cloning of genes encoding viomycin biosynthesis from Streptomyces vinaceus and evidence for involvement of a rare oxygenase Gene 2003, 312, 215-224
    • (2003) Gene , vol.312 , pp. 215-224
    • Yin, X.1    Ohare, T.2    Gould, S.J.3    Zabriskie, T.M.4
  • 3
    • 34547580793 scopus 로고    scopus 로고
    • Biosynthesis of (R)-β-tyrosine and its incorporation into the highly cytotoxic chondramides produced by Chondromyces crocatus
    • Rachid, S.; Krug, D.; Weissman, K. J.; Müller, R. Biosynthesis of (R)-β-tyrosine and its incorporation into the highly cytotoxic chondramides produced by Chondromyces crocatus J. Biol. Chem. 2007, 282, 21810-21817
    • (2007) J. Biol. Chem. , vol.282 , pp. 21810-21817
    • Rachid, S.1    Krug, D.2    Weissman, K.J.3    Müller, R.4
  • 4
    • 0347721776 scopus 로고    scopus 로고
    • Biosynthesis of the enediyne antitumor antibiotic C-1027
    • Liu, W.; Christenson, S. D.; Standage, S.; Shen, B. Biosynthesis of the enediyne antitumor antibiotic C-1027 Science 2002, 297, 1170-1173
    • (2002) Science , vol.297 , pp. 1170-1173
    • Liu, W.1    Christenson, S.D.2    Standage, S.3    Shen, B.4
  • 5
    • 0015211527 scopus 로고
    • Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia
    • Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. Plant antitumor agents. VI. Isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia J. Am. Chem. Soc. 1971, 93, 2325-2327
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2325-2327
    • Wani, M.C.1    Taylor, H.L.2    Wall, M.E.3    Coggon, P.4    McPhail, A.T.5
  • 6
    • 0032829866 scopus 로고    scopus 로고
    • Chemical process synthesis of β-amino acids and esters
    • references cited herein
    • Abdel-Magid, A. F.; Cohen, J. H.; Maryanoff, C. A. Chemical process synthesis of β-amino acids and esters Curr. Med. Chem. 1999, 6, 955-970 and references cited herein
    • (1999) Curr. Med. Chem. , vol.6 , pp. 955-970
    • Abdel-Magid, A.F.1    Cohen, J.H.2    Maryanoff, C.A.3
  • 7
    • 47049104390 scopus 로고    scopus 로고
    • Catalytic synthesis of β3-amino acid derivatives from α-amino acids
    • Byrne, C. M.; Church, T. L.; Kramer, J. W.; Coates, G. W. Catalytic synthesis of β3-amino acid derivatives from α-amino acids Angew. Chem., Int. Ed. 2008, 47, 3979-3983
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3979-3983
    • Byrne, C.M.1    Church, T.L.2    Kramer, J.W.3    Coates, G.W.4
  • 8
    • 34948842371 scopus 로고    scopus 로고
    • Preparation of the β3-homoselenocysteine derivatives Fmoc-β3hSec(PMB)-OH and Boc-β3hSec(PMB)-OH for solution and solid-phase-peptide synthesis and selenoligation
    • Flögel, O.; Casi, G.; Hilvert, D.; Seebach, D. Preparation of the β3-homoselenocysteine derivatives Fmoc-β3hSec(PMB)-OH and Boc-β3hSec(PMB)-OH for solution and solid-phase-peptide synthesis and selenoligation Helv. Chim. Acta 2007, 90, 1651-1666
    • (2007) Helv. Chim. Acta , vol.90 , pp. 1651-1666
    • Flögel, O.1    Casi, G.2    Hilvert, D.3    Seebach, D.4
  • 9
    • 3042825147 scopus 로고    scopus 로고
    • Kowalski ester homologation. Application to the synthesis of β-amino esters
    • Gray, D.; Concellón, C.; Gallagher, T. Kowalski ester homologation. Application to the synthesis of β-amino esters J. Org. Chem. 2004, 69, 4849-4851
    • (2004) J. Org. Chem. , vol.69 , pp. 4849-4851
    • Gray, D.1    Concellón, C.2    Gallagher, T.3
  • 10
    • 68949114275 scopus 로고    scopus 로고
    • Catalytic asymmetric direct Mannich reaction: A powerful tool for the synthesis of α,β-diamino acids
    • Arrayás, R. G.; Carretero, J. C. Catalytic asymmetric direct Mannich reaction: A powerful tool for the synthesis of α,β-diamino acids Chem. Soc. Rev. 2009, 38, 1940-1948
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 1940-1948
    • Arrayás, R.G.1    Carretero, J.C.2
  • 11
    • 70350506798 scopus 로고    scopus 로고
    • Organocatalytic asymmetric aza-Michael additions
    • Enders, D.; Wang, C.; Liebich, J. X. Organocatalytic asymmetric aza-Michael additions Chem. - Eur. J. 2009, 15, 11058-11076
    • (2009) Chem. - Eur. J. , vol.15 , pp. 11058-11076
    • Enders, D.1    Wang, C.2    Liebich, J.X.3
  • 12
    • 35348920033 scopus 로고    scopus 로고
    • Organocatalytic synthesis of β-alkylaspartates via β-lactone ring opening
    • Armstrong, A.; Geldart, S. P.; Jenner, C. R.; Scutt, J. N. Organocatalytic synthesis of β-alkylaspartates via β-lactone ring opening J. Org. Chem. 2007, 72, 8091-8094
    • (2007) J. Org. Chem. , vol.72 , pp. 8091-8094
    • Armstrong, A.1    Geldart, S.P.2    Jenner, C.R.3    Scutt, J.N.4
  • 13
    • 0037178970 scopus 로고    scopus 로고
    • Divergent reaction pathways in amine additions to β-lactone electrophiles. An application to β-peptide synthesis
    • Nelson, S. G.; Spencer, K. L.; Cheung, W. S.; Mamie, S. J. Divergent reaction pathways in amine additions to β-lactone electrophiles. An application to β-peptide synthesis Tetrahedron 2002, 58, 7081-7091
    • (2002) Tetrahedron , vol.58 , pp. 7081-7091
    • Nelson, S.G.1    Spencer, K.L.2    Cheung, W.S.3    Mamie, S.J.4
  • 14
    • 0034599875 scopus 로고    scopus 로고
    • Enantioselective β-amino acid synthesis based on catalyzed asymmetric acyl halide-aldehyde cyclocondensation reactions
    • Nelson, S. G.; Spencer, K. L. Enantioselective β-amino acid synthesis based on catalyzed asymmetric acyl halide-aldehyde cyclocondensation reactions Angew. Chem., Int. Ed. 2000, 39, 1323-1325
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 1323-1325
    • Nelson, S.G.1    Spencer, K.L.2
  • 15
    • 0037070622 scopus 로고    scopus 로고
    • Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles
    • Guerin, D. J.; Miller, S. J. Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles J. Am. Chem. Soc. 2002, 124, 2134-2136
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2134-2136
    • Guerin, D.J.1    Miller, S.J.2
  • 16
    • 0034675660 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of azide to α,β-unsaturated carbonyl compounds catalyzed by simple peptides
    • Horstmann, T. E.; Guerin, D. J.; Miller, S. J. Asymmetric conjugate addition of azide to α,β-unsaturated carbonyl compounds catalyzed by simple peptides Angew. Chem., Int. Ed. 2000, 39, 3635-3638
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3635-3638
    • Horstmann, T.E.1    Guerin, D.J.2    Miller, S.J.3
  • 17
    • 0033533638 scopus 로고    scopus 로고
    • Amine-catalyzed addition of azide ion to α,β-unsaturated carbonyl compounds
    • Guerin, D. J.; Horstmann, T. E.; Miller, S. J. Amine-catalyzed addition of azide ion to α,β-unsaturated carbonyl compounds Org. Lett. 1999, 1, 1107-1109
    • (1999) Org. Lett. , vol.1 , pp. 1107-1109
    • Guerin, D.J.1    Horstmann, T.E.2    Miller, S.J.3
  • 18
    • 84858788491 scopus 로고    scopus 로고
    • Preparation and use of polystyryl-DABCOF2: An efficient recoverable and reusable catalyst for β-azidation of α,β-unsaturated ketones in water
    • Angelini, T.; Lanari, D.; Maggi, R.; Pizzo, F.; Sartori, G.; Vaccaro, L. Preparation and use of polystyryl-DABCOF2: An efficient recoverable and reusable catalyst for β-azidation of α,β-unsaturated ketones in water Adv. Synth. Catal. 2012, 354, 908-916
    • (2012) Adv. Synth. Catal. , vol.354 , pp. 908-916
    • Angelini, T.1    Lanari, D.2    Maggi, R.3    Pizzo, F.4    Sartori, G.5    Vaccaro, L.6
  • 19
    • 33845514121 scopus 로고    scopus 로고
    • Amberlite IRA900N3 as a new catalyst for the azidation of α,β-unsaturated ketones under solvent-free conditions
    • Castrica, L.; Fringuelli, F.; Gregoli, L.; Pizzo, F.; Vaccaro, L. Amberlite IRA900N3 as a new catalyst for the azidation of α,β-unsaturated ketones under solvent-free conditions J. Org. Chem. 2006, 71, 9536-9539
    • (2006) J. Org. Chem. , vol.71 , pp. 9536-9539
    • Castrica, L.1    Fringuelli, F.2    Gregoli, L.3    Pizzo, F.4    Vaccaro, L.5
  • 20
    • 53849137708 scopus 로고    scopus 로고
    • Amberlite IRA900F as a solid fluoride source for a variety of organic transformations under solvent-free conditions
    • Fringuelli, F.; Lanari, D.; Pizzo, F.; Vaccaro, L. Amberlite IRA900F as a solid fluoride source for a variety of organic transformations under solvent-free conditions Eur. J. Org. Chem. 2008, 3928-3932
    • (2008) Eur. J. Org. Chem. , pp. 3928-3932
    • Fringuelli, F.1    Lanari, D.2    Pizzo, F.3    Vaccaro, L.4
  • 21
    • 84866023041 scopus 로고    scopus 로고
    • A protocol for accessing the β-azidation of α,β-unsaturated carboxylic acids
    • Angelini, T.; Bonollo, S.; Lanari, D.; Pizzo, F.; Vaccaro, L. A protocol for accessing the β-azidation of α,β-unsaturated carboxylic acids Org. Lett. 2012, 14, 4610-4613
    • (2012) Org. Lett. , vol.14 , pp. 4610-4613
    • Angelini, T.1    Bonollo, S.2    Lanari, D.3    Pizzo, F.4    Vaccaro, L.5
  • 22
    • 0347933770 scopus 로고    scopus 로고
    • Catalysis and pollution prevention
    • (London)
    • Sheldon, R. A. Catalysis and pollution prevention. Chem. Ind. (London) 1997, 12-15.
    • (1997) Chem. Ind. , pp. 12-15
    • Sheldon, R.A.1
  • 23
    • 36348937198 scopus 로고    scopus 로고
    • The e Factor: Fifteen years on
    • Sheldon, R. A. The E Factor: Fifteen years on Green Chem. 2007, 9, 1273-1283
    • (2007) Green Chem. , vol.9 , pp. 1273-1283
    • Sheldon, R.A.1
  • 24
    • 38049000664 scopus 로고    scopus 로고
    • A new rationale of reaction metrics for green chemistry. Mathematical expression of the environmental impact factor of chemical processes
    • Augé, J. A new rationale of reaction metrics for green chemistry. Mathematical expression of the environmental impact factor of chemical processes Green Chem. 2008, 10, 225-231
    • (2008) Green Chem. , vol.10 , pp. 225-231
    • Augé, J.1
  • 25
    • 47549112707 scopus 로고    scopus 로고
    • E-factors, green chemistry and catalysis: An odyssey
    • Sheldon, R. A. E-factors, green chemistry and catalysis: An odyssey Chem. Commun. 2008, 3352-3365
    • (2008) Chem. Commun. , pp. 3352-3365
    • Sheldon, R.A.1
  • 26
    • 84863717561 scopus 로고    scopus 로고
    • Cu(II) triflate-sodium dodecyl sulfate catalyzed preparation of 1,2-diphenyl-2,3-dihydro-4-pyridones in acidic aqueous medium
    • Lanari, D.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Cu(II) triflate-sodium dodecyl sulfate catalyzed preparation of 1,2-diphenyl-2,3-dihydro-4-pyridones in acidic aqueous medium Synthesis 2012, 2181-2184
    • (2012) Synthesis , pp. 2181-2184
    • Lanari, D.1    Piermatti, O.2    Pizzo, F.3    Vaccaro, L.4
  • 27
    • 79961032702 scopus 로고    scopus 로고
    • Supported l -proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition
    • Calogero, S.; Lanari, D.; Orrù, M.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Supported l -proline on zirconium phosphates methyl and/or phenyl phosphonates as heterogeneous organocatalysts for direct asymmetric aldol addition J. Catal. 2011, 282, 112-119
    • (2011) J. Catal. , vol.282 , pp. 112-119
    • Calogero, S.1    Lanari, D.2    Orrù, M.3    Piermatti, O.4    Pizzo, F.5    Vaccaro, L.6
  • 28
    • 79955590448 scopus 로고    scopus 로고
    • Sc(III)-catalyzed enantioselective addition of thiols to α,β-unsaturated ketones in neutral water
    • Bonollo, S.; Lanari, D.; Pizzo, F.; Vaccaro, L. Sc(III)-catalyzed enantioselective addition of thiols to α,β-unsaturated ketones in neutral water Org. Lett. 2011, 13, 2150-2152
    • (2011) Org. Lett. , vol.13 , pp. 2150-2152
    • Bonollo, S.1    Lanari, D.2    Pizzo, F.3    Vaccaro, L.4
  • 30
    • 79955867707 scopus 로고    scopus 로고
    • Diastereoselective three-step route to o -(6-nitrocyclohex-3-en-1-yl)phenol and tetrahydro-6H-benzo[c]chromen-6-ol derivatives from salicylaldehydes
    • Lanari, D.; Ballini, R.; Palmieri, A.; Pizzo, F.; Vaccaro, L. Diastereoselective three-step route to o -(6-nitrocyclohex-3-en-1-yl)phenol and tetrahydro-6H-benzo[c]chromen-6-ol derivatives from salicylaldehydes Eur. J. Org. Chem. 2011, 2874-2884
    • (2011) Eur. J. Org. Chem. , pp. 2874-2884
    • Lanari, D.1    Ballini, R.2    Palmieri, A.3    Pizzo, F.4    Vaccaro, L.5
  • 31
    • 77954568163 scopus 로고    scopus 로고
    • An E-factor minimized protocol for the preparation of methyl β-hydroxy esters
    • Fringuelli, F.; Lanari, D.; Pizzo, F.; Vaccaro, L. An E-factor minimized protocol for the preparation of methyl β-hydroxy esters Green Chem. 2010, 12, 1301-1305
    • (2010) Green Chem. , vol.12 , pp. 1301-1305
    • Fringuelli, F.1    Lanari, D.2    Pizzo, F.3    Vaccaro, L.4
  • 32
    • 78349257365 scopus 로고    scopus 로고
    • 2- tert -Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP) as an efficient recoverable and reusable catalyst for the phenolysis of epoxides under solvent-free conditions
    • Zvagulis, A.; Bonollo, S.; Lanari, D.; Pizzo, F.; Vaccaro, L. 2- tert -Butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene (PS-BEMP) as an efficient recoverable and reusable catalyst for the phenolysis of epoxides under solvent-free conditions Adv. Synth. Catal. 2010, 352, 2489-2496
    • (2010) Adv. Synth. Catal. , vol.352 , pp. 2489-2496
    • Zvagulis, A.1    Bonollo, S.2    Lanari, D.3    Pizzo, F.4    Vaccaro, L.5
  • 33
    • 53949091249 scopus 로고    scopus 로고
    • Polystyryl-BEMP as an efficient recyclable catalyst for the nucleophilic addition of nitroalkanes to α,β-unsaturated carbonyl compounds under solvent-free conditions
    • Ballini, R.; Barboni, L.; Castrica, L.; Fringuelli, F.; Lanari, D.; Pizzo, F.; Vaccaro, L. Polystyryl-BEMP as an efficient recyclable catalyst for the nucleophilic addition of nitroalkanes to α,β-unsaturated carbonyl compounds under solvent-free conditions Adv. Synth. Catal. 2008, 350, 1218-1224
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1218-1224
    • Ballini, R.1    Barboni, L.2    Castrica, L.3    Fringuelli, F.4    Lanari, D.5    Pizzo, F.6    Vaccaro, L.7
  • 34
    • 33745560785 scopus 로고    scopus 로고
    • [AlCl3 + 2THF]: A new and efficient catalytic system for Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions
    • Fringuelli, F.; Girotti, R.; Pizzo, F.; Vaccaro, L. [AlCl3 + 2THF]: A new and efficient catalytic system for Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions Org. Lett. 2006, 8, 2487-2489
    • (2006) Org. Lett. , vol.8 , pp. 2487-2489
    • Fringuelli, F.1    Girotti, R.2    Pizzo, F.3    Vaccaro, L.4
  • 35
    • 84882588564 scopus 로고    scopus 로고
    • A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols
    • Ballerini, E.; Crotti, P.; Frau, I.; Lanari, D.; Pizzo, F.; Vaccaro, L. A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols Green Chem. 2013, 15, 2394-2400
    • (2013) Green Chem. , vol.15 , pp. 2394-2400
    • Ballerini, E.1    Crotti, P.2    Frau, I.3    Lanari, D.4    Pizzo, F.5    Vaccaro, L.6
  • 36
    • 84880836865 scopus 로고    scopus 로고
    • Palladium supported on cross-linked imidazolium network on silica as highly sustainable catalysts for the Suzuki reaction under flow conditions
    • Pavia, C.; Ballerini, E.; Bivona, L. A.; Giacalone, F.; Aprile, C.; Vaccaro, L.; Gruttadauria, M. Palladium supported on cross-linked imidazolium network on silica as highly sustainable catalysts for the Suzuki reaction under flow conditions Adv. Synth. Catal. 2013, 355, 2007-2018
    • (2013) Adv. Synth. Catal. , vol.355 , pp. 2007-2018
    • Pavia, C.1    Ballerini, E.2    Bivona, L.A.3    Giacalone, F.4    Aprile, C.5    Vaccaro, L.6    Gruttadauria, M.7
  • 37
    • 84871733867 scopus 로고    scopus 로고
    • Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls
    • Strappaveccia, G.; Lanari, D.; Gelman, D.; Pizzo, F.; Rosati, O.; Curini, M.; Vaccaro, L. Efficient synthesis of cyanohydrin trimethylsilyl ethers via 1,2-chemoselective cyanosilylation of carbonyls Green Chem. 2013, 15, 199-204
    • (2013) Green Chem. , vol.15 , pp. 199-204
    • Strappaveccia, G.1    Lanari, D.2    Gelman, D.3    Pizzo, F.4    Rosati, O.5    Curini, M.6    Vaccaro, L.7
  • 38
    • 84881102521 scopus 로고    scopus 로고
    • E-Factor minimized hydrophosphonylation of aldehydes catalyzed by polystyryl-BEMP under solvent-free conditions
    • Angelini, T.; Bonollo, S.; Lanari, D.; Pizzo, F.; Vaccaro, L. E-Factor minimized hydrophosphonylation of aldehydes catalyzed by polystyryl-BEMP under solvent-free conditions Org. Biomol. Chem. 2013, 11, 5042-5046
    • (2013) Org. Biomol. Chem. , vol.11 , pp. 5042-5046
    • Angelini, T.1    Bonollo, S.2    Lanari, D.3    Pizzo, F.4    Vaccaro, L.5
  • 39
    • 84857164125 scopus 로고    scopus 로고
    • E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds
    • Bonollo, S.; Lanari, D.; Longo, J. M.; Vaccaro, L. E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds Green Chem. 2012, 14, 164-169
    • (2012) Green Chem. , vol.14 , pp. 164-169
    • Bonollo, S.1    Lanari, D.2    Longo, J.M.3    Vaccaro, L.4
  • 41
    • 79961218749 scopus 로고    scopus 로고
    • Deciding whether to go with the flow: Evaluating the merits of flow reactors for synthesis
    • Hartman, R. L.; McMullen, J. P.; Jensen, K. F. Deciding whether to go with the flow: Evaluating the merits of flow reactors for synthesis Angew. Chem., Int. Ed. 2011, 50, 7502-7519
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7502-7519
    • Hartman, R.L.1    McMullen, J.P.2    Jensen, K.F.3
  • 42
    • 79551614063 scopus 로고    scopus 로고
    • Continuous flow multi-step organic synthesis
    • Webb, D.; Jamison, T. F. Continuous flow multi-step organic synthesis Chem. Sci. 2010, 1, 675-680
    • (2010) Chem. Sci. , vol.1 , pp. 675-680
    • Webb, D.1    Jamison, T.F.2
  • 43
    • 78149427210 scopus 로고    scopus 로고
    • Heterogeneous catalytic synthesis using microreactor technology
    • Frost, C. G.; Mutton, L. Heterogeneous catalytic synthesis using microreactor technology Green Chem. 2010, 12, 1687-1703
    • (2010) Green Chem. , vol.12 , pp. 1687-1703
    • Frost, C.G.1    Mutton, L.2
  • 44
    • 34447109277 scopus 로고    scopus 로고
    • Greener approaches to organic synthesis using microreactor technology
    • Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Greener approaches to organic synthesis using microreactor technology Chem. Rev. 2007, 107, 2300-2318
    • (2007) Chem. Rev. , vol.107 , pp. 2300-2318
    • Mason, B.P.1    Price, K.E.2    Steinbacher, J.L.3    Bogdan, A.R.4    McQuade, D.T.5
  • 45
    • 84922776427 scopus 로고    scopus 로고
    • A comparative approach to the most sustainable protocol for the β-azidation of α,β-unsaturated ketones and acids
    • Andraos, J.; Ballerini, E.; Vaccaro, L. A comparative approach to the most sustainable protocol for the β-azidation of α,β-unsaturated ketones and acids Green Chem. 2015, 17, 913-925
    • (2015) Green Chem. , vol.17 , pp. 913-925
    • Andraos, J.1    Ballerini, E.2    Vaccaro, L.3
  • 46
    • 65949109263 scopus 로고    scopus 로고
    • Global green chemistry metrics analysis algorithm and spreadsheets: Evaluation of the material efficiency of synthesis plans for Oseltamivir phosphate (Tamiflu) as a test case
    • Andraos, J. Global green chemistry metrics analysis algorithm and spreadsheets: Evaluation of the material efficiency of synthesis plans for Oseltamivir phosphate (Tamiflu) as a test case Org. Process Res. Dev. 2009, 13, 161-185
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 161-185
    • Andraos, J.1
  • 47
    • 79960492760 scopus 로고    scopus 로고
    • Using the right green yardstick: Why process mass intensity is used in the pharmaceutical industry to drive more sustainable processes
    • Jimenez-Gonzalez, C.; Ponder, C. S.; Broxterman, Q. B.; Manley, J. B. Using the right green yardstick: why process mass intensity is used in the pharmaceutical industry to drive more sustainable processes Org. Process Res. Dev. 2011, 15, 912-917
    • (2011) Org. Process Res. Dev. , vol.15 , pp. 912-917
    • Jimenez-Gonzalez, C.1    Ponder, C.S.2    Broxterman, Q.B.3    Manley, J.B.4
  • 48
    • 0033039667 scopus 로고    scopus 로고
    • A facile procedure for reduction of azides to amines with aluminium triiodide
    • Barua, A.; Bez, G.; Barua, N. C. A facile procedure for reduction of azides to amines with aluminium triiodide Indian J. Chem. B 1999, 38, 128-129
    • (1999) Indian J. Chem. B , vol.38 , pp. 128-129
    • Barua, A.1    Bez, G.2    Barua, N.C.3
  • 49
    • 0031562042 scopus 로고    scopus 로고
    • Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine
    • Huang, Y.; Zhang, Y.; Wang, Y. Facile reduction of azides to the corresponding amines with metallic samarium and catalytic amount of iodine Tetrahedron Lett. 1997, 38, 1065-1066
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1065-1066
    • Huang, Y.1    Zhang, Y.2    Wang, Y.3
  • 50
    • 0030771180 scopus 로고    scopus 로고
    • Iodotrimethylsilane: A mild and efficient reagent for the reduction of azides to amines
    • Kamal, A.; Rao, N. V.; Laxman, E. Iodotrimethylsilane: A mild and efficient reagent for the reduction of azides to amines Tetrahedron Lett. 1997, 38, 6945-6948
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6945-6948
    • Kamal, A.1    Rao, N.V.2    Laxman, E.3
  • 51
    • 0002734624 scopus 로고    scopus 로고
    • The efficient chemoselective reduction of azides to primary amines
    • Boruah, A.; Baruah, M.; Prajapati, D.; Sandhu, J. S. The efficient chemoselective reduction of azides to primary amines Synlett 1997, 1253-1254
    • (1997) Synlett , pp. 1253-1254
    • Boruah, A.1    Baruah, M.2    Prajapati, D.3    Sandhu, J.S.4
  • 53
    • 0028204919 scopus 로고
    • Facile reduction of azides with sodium borohydride/copper(II) sulphate system
    • Rao, H. S. P.; Siva, P. Facile reduction of azides with sodium borohydride/copper(II) sulphate system Synth. Commun. 1994, 24, 549-555
    • (1994) Synth. Commun. , vol.24 , pp. 549-555
    • Rao, H.S.P.1    Siva, P.2
  • 54
    • 0027520152 scopus 로고
    • Reduction of azides to amines with borohydride exchange resin - Nickel acetate
    • Yoon, N. M.; Choi, J.; Shon, Y. S. Reduction of azides to amines with borohydride exchange resin-nickel acetate Synth. Commun. 1993, 23, 3047-3053
    • (1993) Synth. Commun. , vol.23 , pp. 3047-3053
    • Yoon, N.M.1    Choi, J.2    Shon, Y.S.3
  • 55
    • 33751158821 scopus 로고
    • Reduction of azides with zinc borohydride
    • Ranu, B. C.; Sarkar, A.; Chakraborty, R. Reduction of azides with zinc borohydride J. Org. Chem. 1994, 59, 4114-4116
    • (1994) J. Org. Chem. , vol.59 , pp. 4114-4116
    • Ranu, B.C.1    Sarkar, A.2    Chakraborty, R.3
  • 56
    • 0026598233 scopus 로고
    • Reduction of aroyl azides with sodium borohydride/nickel(II) chloride
    • Rao, H. S. P.; Reddy, K. S.; Turnbull, K.; Borchers, V. Reduction of aroyl azides with sodium borohydride/nickel(II) chloride Synth. Commun. 1992, 22, 1339-1343
    • (1992) Synth. Commun. , vol.22 , pp. 1339-1343
    • Rao, H.S.P.1    Reddy, K.S.2    Turnbull, K.3    Borchers, V.4
  • 57
    • 33845553576 scopus 로고
    • Sodium borohydride reactions under phase-transfer conditions: Reduction of azides to amines
    • Rolla, F. Sodium borohydride reactions under phase-transfer conditions: Reduction of azides to amines J. Org. Chem. 1982, 47, 4327-4329
    • (1982) J. Org. Chem. , vol.47 , pp. 4327-4329
    • Rolla, F.1
  • 58
    • 33845374200 scopus 로고
    • Synthetically useful reactions with metal boride and aluminide catalysts
    • Ganem, B.; Osby, J. O. Synthetically useful reactions with metal boride and aluminide catalysts Chem. Rev. 1986, 86, 763-780
    • (1986) Chem. Rev. , vol.86 , pp. 763-780
    • Ganem, B.1    Osby, J.O.2
  • 59
    • 33845555740 scopus 로고
    • Mechanism of sodium borohydride-cobaltous chloride reductions
    • Heinzman, S. W.; Ganem, B. Mechanism of sodium borohydride-cobaltous chloride reductions J. Am. Chem. Soc. 1982, 104, 6801-6802
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 6801-6802
    • Heinzman, S.W.1    Ganem, B.2
  • 60
    • 0034033001 scopus 로고    scopus 로고
    • Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water
    • Fringuelli, F.; Pizzo, F.; Vaccaro, L. Cobalt(II) chloride-catalyzed chemoselective sodium borohydride reduction of azides in water Synthesis 2000, 646-650
    • (2000) Synthesis , pp. 646-650
    • Fringuelli, F.1    Pizzo, F.2    Vaccaro, L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.