메뉴 건너뛰기




Volumn 39, Issue 5, 2009, Pages 792-798

Addition of allylindium reagents to α- iminotrifluoroethylphosphonates: Synthesis of CF3-containing α-aminoalkylphosphonates

Author keywords

iminotrifluoroethylphosphonates; aminoalkylphosphonates; Allylation; Indium

Indexed keywords

ALLYL COMPOUND; ALPHA AMINOALKYLPHOSPHONATE DERIVATIVE; ALPHA IMINOTRIFLUOROETHYLPHOSPHATE; INDIUM; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 61649116455     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802431156     Document Type: Article
Times cited : (5)

References (39)
  • 2
    • 13344250452 scopus 로고    scopus 로고
    • Noncovalent binding between guanidinium and anionic groups: Focus on biological and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues
    • (b) Schug, K. A.; Lindner, W. Noncovalent binding between guanidinium and anionic groups: Focus on biological and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues. Chem. Rev. 2005, 105, 67-114;
    • (2005) Chem. Rev , vol.105 , pp. 67-114
    • Schug, K.A.1    Lindner, W.2
  • 3
    • 11144313152 scopus 로고    scopus 로고
    • Synthetic methods for azaheterocyclic phosphonates and their biological activity
    • (c) Moonen, K.; Laureyn, I.; Stevens, C. V. Synthetic methods for azaheterocyclic phosphonates and their biological activity. Chem. Rev. 2004, 104, 6177-6216;
    • (2004) Chem. Rev , vol.104 , pp. 6177-6216
    • Moonen, K.1    Laureyn, I.2    Stevens, C.V.3
  • 6
    • 0001624368 scopus 로고    scopus 로고
    • Aminophosphonic acids of potential medical importance
    • (b) Kafarski, P.; Lejczak, B. Aminophosphonic acids of potential medical importance. Curr. Med. Chem. 2001, 1, 301-312;
    • (2001) Curr. Med. Chem , vol.1 , pp. 301-312
    • Kafarski, P.1    Lejczak, B.2
  • 7
    • 0024409372 scopus 로고
    • Renin inhibitors: Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond
    • (c) Allen, M. C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J. M. Renin inhibitors: Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J. Med. Chem. 1989, 32, 1652-1661;
    • (1989) J. Med. Chem , vol.32 , pp. 1652-1661
    • Allen, M.C.1    Fuhrer, W.2    Tuck, B.3    Wade, R.4    Wood, J.M.5
  • 8
    • 0023780644 scopus 로고
    • Synthesis of alpha- and gamma-alkyl-substituted phosphinothricins: Potent new inhibitors of glutamine synthetase
    • (d) Logusch, E. W.; Walker, D. M.; McDonald, J. F.; Leo, G. C.; Grang, J. E. Synthesis of alpha- and gamma-alkyl-substituted phosphinothricins: Potent new inhibitors of glutamine synthetase. J. Org. Chem. 1988, 53, 4069-4074;
    • (1988) J. Org. Chem , vol.53 , pp. 4069-4074
    • Logusch, E.W.1    Walker, D.M.2    McDonald, J.F.3    Leo, G.C.4    Grang, J.E.5
  • 9
    • 0023277991 scopus 로고
    • Phosphorus amino acid analogs as inhibitors of leucine aminopeptidase
    • (e) Giannousis, P. P.; Bartlett, P. A. Phosphorus amino acid analogs as inhibitors of leucine aminopeptidase. J. Med. Chem. 1987, 30, 1603-1609.
    • (1987) J. Med. Chem , vol.30 , pp. 1603-1609
    • Giannousis, P.P.1    Bartlett, P.A.2
  • 10
  • 11
    • 0032550658 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of an inhibitor bridged between P2 and P1
    • (b) Smith, W. W.; Bartlett, P. A. Design, synthesis, and evaluation of an inhibitor bridged between P2 and P1. J. Am. Chem. Soc. 1998, 120, 4622-4628;
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 4622-4628
    • Smith, W.W.1    Bartlett, P.A.2
  • 12
    • 0022577081 scopus 로고
    • Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)-phosphonic acid
    • (c) Atherton, F. R.; Hassel, C. H.; Lambert, R. W. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)-phosphonic acid. J. Med. Chem. 1986, 29, 29-40.
    • (1986) J. Med. Chem , vol.29 , pp. 29-40
    • Atherton, F.R.1    Hassel, C.H.2    Lambert, R.W.3
  • 13
    • 0001838111 scopus 로고
    • How to find a great herbiaide
    • (a) Barder, A. How to find a great herbiaide. Aldrichim Acta 1988, 21, 15;
    • (1988) Aldrichim Acta , vol.21 , pp. 15
    • Barder, A.1
  • 15
    • 0034618163 scopus 로고    scopus 로고
    • Synthesis of aminophosphonate haptens for an aminoacylation reaction between methyl glucoside and α, β-alanyl ester
    • (a) Lintunen, T.; Yli-Kauhalouoma, J. T. Synthesis of aminophosphonate haptens for an aminoacylation reaction between methyl glucoside and α, β-alanyl ester. Bioorg. Med. Chem. Lett. 2000, 10, 1749-1750;
    • (2000) Bioorg. Med. Chem. Lett , vol.10 , pp. 1749-1750
    • Lintunen, T.1    Yli-Kauhalouoma, J.T.2
  • 17
    • 0027982561 scopus 로고
    • Peptide bond formation via catalytic antibodies: Synthesis of a novel phosphonate diester hapten
    • (c) Smith III, A. B.; Taylor, C. M.; Venkovic, S. J.; Hirschmann, R. Peptide bond formation via catalytic antibodies: Synthesis of a novel phosphonate diester hapten. Tetrahedron Lett. 1994, 37, 6853-6856.
    • (1994) Tetrahedron Lett , vol.37 , pp. 6853-6856
    • Smith III, A.B.1    Taylor, C.M.2    Venkovic, S.J.3    Hirschmann, R.4
  • 19
    • 0034926661 scopus 로고    scopus 로고
    • Fluorine substituent effects on bioactivity
    • (b) Smart, B. E. Fluorine substituent effects on bioactivity. J. Fluorine Chem. 2001, 109, 3-11;
    • (2001) J. Fluorine Chem , vol.109 , pp. 3-11
    • Smart, B.E.1
  • 20
    • 0036882589 scopus 로고    scopus 로고
    • Important fluorinated drugs in experimental and clinical use
    • (c) Ismail, F. M. D. Important fluorinated drugs in experimental and clinical use. J. Fluorine Chem. 2002, 118, 27-33.
    • (2002) J. Fluorine Chem , vol.118 , pp. 27-33
    • Ismail, F.M.D.1
  • 21
    • 0033930445 scopus 로고    scopus 로고
    • 3-Substituted phosphorus containing analogs of α-amino acids: Novel six- and seven-membered α-amino phosphonates via ring closing metathesis with LnRu=C=C=CR2 precatalyst
    • 3-Substituted phosphorus containing analogs of α-amino acids: Novel six- and seven-membered α-amino phosphonates via ring closing metathesis with LnRu=C=C=CR2 precatalyst. Synlett 2000, 1031-1033;
    • (2000) Synlett , pp. 1031-1033
    • Osipov, S.N.1    Artyushin, O.I.2    Kolomiets, A.F.3    Bruneau, C.4    Dixneuf, P.H.5
  • 22
    • 0040182778 scopus 로고    scopus 로고
    • New α-trifluoromethyl-substituted α-amino phosphonates
    • (b) Osipov, S. N.; Artyushin, O. I.; Kolomiets, A. F. New α-trifluoromethyl-substituted α-amino phosphonates. Mendeleev Commun. 2000, 10, 192;
    • (2000) Mendeleev Commun , vol.10 , pp. 192
    • Osipov, S.N.1    Artyushin, O.I.2    Kolomiets, A.F.3
  • 23
    • 0034510779 scopus 로고    scopus 로고
    • A facile asymmetric synthesis of 1-amino-2,2,2-trifluoroethanephosphonic acid
    • (c) Xiao, J.; Zhang, X.; Yuan, C. A facile asymmetric synthesis of 1-amino-2,2,2-trifluoroethanephosphonic acid. Heteroatom. Chem. 2000, 11, 536-540;
    • (2000) Heteroatom. Chem , vol.11 , pp. 536-540
    • Xiao, J.1    Zhang, X.2    Yuan, C.3
  • 24
    • 0036160122 scopus 로고    scopus 로고
    • Synthesis of phosphorylated 1,3,5-oxadiazines via N-acetyltrifluoroacetimidoylphosphonstes
    • (d) Onys'ko, P. P.; Sinitsa, O. A.; Pirozhenko, V. V.; Chernega, A. N. Synthesis of phosphorylated 1,3,5-oxadiazines via N-acetyltrifluoroacetimidoylphosphonstes. Heteroatom. Chem. 2002, 13, 22-26;
    • (2002) Heteroatom. Chem , vol.13 , pp. 22-26
    • Onys'ko, P.P.1    Sinitsa, O.A.2    Pirozhenko, V.V.3    Chernega, A.N.4
  • 25
    • 34548685341 scopus 로고    scopus 로고
    • α-Iminotrifluoroethylphosphonates: The first representatives of N-H imidoyl phonsphonates
    • (e) Rassukana, Y. V.; Kolotylo, M. V.; Sinitsa, O. A.; Pirozhenko, V. V.; Onys'ko, P. P. α-Iminotrifluoroethylphosphonates: The first representatives of N-H imidoyl phonsphonates. Synthesis 2007, 2627-2630.
    • (2007) Synthesis , pp. 2627-2630
    • Rassukana, Y.V.1    Kolotylo, M.V.2    Sinitsa, O.A.3    Pirozhenko, V.V.4    Onys'ko, P.P.5
  • 26
    • 0033543497 scopus 로고    scopus 로고
    • Organic syntheses using indium-mediated and catalyzed reactions in aqueous media
    • For reviews on indium-mediated reactions, see a
    • For reviews on indium-mediated reactions, see (a) Li, C. J.; Chan, T. H. Organic syntheses using indium-mediated and catalyzed reactions in aqueous media. Tetrahedron 1999, 55, 11149-11176;
    • (1999) Tetrahedron , vol.55 , pp. 11149-11176
    • Li, C.J.1    Chan, T.H.2
  • 27
    • 0001275138 scopus 로고    scopus 로고
    • Organometallic-type reactions in aqueous media mediated by indium: Application to the synthesis of carbohydrates
    • (b) Chan, T. H.; Isaac, M. B. Organometallic-type reactions in aqueous media mediated by indium: Application to the synthesis of carbohydrates. Pure Appl. Chem. 1996, 68, 919-924;
    • (1996) Pure Appl. Chem , vol.68 , pp. 919-924
    • Chan, T.H.1    Isaac, M.B.2
  • 28
    • 0037571395 scopus 로고
    • Synthetic organoindium chemistry: What makes indium so appealing?
    • (c) Cintas, P. Synthetic organoindium chemistry: What makes indium so appealing? Synlett 1995, 1087-1096.
    • (1995) Synlett , pp. 1087-1096
    • Cintas, P.1
  • 29
    • 34248221504 scopus 로고    scopus 로고
    • Asymmetric electrophilic fluorination of α-cyanoalkylphosphonates catalyzed by chiral palladium complexes
    • (a) Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Asymmetric electrophilic fluorination of α-cyanoalkylphosphonates catalyzed by chiral palladium complexes. Synlett 2007, 1135-1138;
    • (2007) Synlett , pp. 1135-1138
    • Kang, Y.K.1    Cho, M.J.2    Kim, S.M.3    Kim, D.Y.4
  • 30
    • 38049135168 scopus 로고    scopus 로고
    • Catalytic enantioselective fluorination reactions of α-cyanoacetates and α-cyanophosphonates using chiral palladium complexes
    • (b) Kim, S. M.; Kang, Y. K.; Cho, M. J.; Mang, J. Y.; Kim, D. Y. Catalytic enantioselective fluorination reactions of α-cyanoacetates and α-cyanophosphonates using chiral palladium complexes. Bull. Korean Chem. Soc. 2007, 28, 2435-2441;
    • (2007) Bull. Korean Chem. Soc , vol.28 , pp. 2435-2441
    • Kim, S.M.1    Kang, Y.K.2    Cho, M.J.3    Mang, J.Y.4    Kim, D.Y.5
  • 31
    • 33645234367 scopus 로고    scopus 로고
    • Asymmetric electrophilic fluorination of β-keto phosphonates in ionic liquid media catalyzed by chiral palladium complexes
    • (c) Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J.Y.; Kim, D. Y. Asymmetric electrophilic fluorination of β-keto phosphonates in ionic liquid media catalyzed by chiral palladium complexes. Bull. Korean Chem. Soc. 2006, 27, 423-425;
    • (2006) Bull. Korean Chem. Soc , vol.27 , pp. 423-425
    • Kim, S.M.1    Kang, Y.K.2    Lee, K.3    Mang, J.Y.4    Kim, D.Y.5
  • 32
    • 20544442026 scopus 로고    scopus 로고
    • Catalytic enantioselective fluorination and amination of β-keto phosphonates catalyzed by chiral palladium complexes
    • (d) Kim, S. M.; Kim, H. R.; Kim, D. Y. Catalytic enantioselective fluorination and amination of β-keto phosphonates catalyzed by chiral palladium complexes. Org. Lett. 2005, 7, 2309-2311;
    • (2005) Org. Lett , vol.7 , pp. 2309-2311
    • Kim, S.M.1    Kim, H.R.2    Kim, D.Y.3
  • 33
    • 0034808929 scopus 로고    scopus 로고
    • Michael addition of N-(diphenylmethylene)aminomethylphosphonate to acrylates using phase transfer catalysis conditions: Synthesis of 1-(N-diphenylmethylene) amino-3-(alkoxycarbonyl)-propylphosphonates
    • (e) Kim, D. Y.; Suh, K. H.; Huh, S. C.; Lee, K. Michael addition of N-(diphenylmethylene)aminomethylphosphonate to acrylates using phase transfer catalysis conditions: Synthesis of 1-(N-diphenylmethylene) amino-3-(alkoxycarbonyl)-propylphosphonates. Synth. Commun. 2001, 31, 3315-3322;
    • (2001) Synth. Commun , vol.31 , pp. 3315-3322
    • Kim, D.Y.1    Suh, K.H.2    Huh, S.C.3    Lee, K.4
  • 34
    • 0033527798 scopus 로고    scopus 로고
    • Acylation of α- fluorophosphonoacetate derivatives using magnesium chloride-triethylamine
    • (f) Kim, D. Y.; Lee, Y. M.; Choi, Y. J. Acylation of α- fluorophosphonoacetate derivatives using magnesium chloride-triethylamine. Tetrahedron 1999, 55, 12983-12990;
    • (1999) Tetrahedron , vol.55 , pp. 12983-12990
    • Kim, D.Y.1    Lee, Y.M.2    Choi, Y.J.3
  • 35
    • 0030886048 scopus 로고    scopus 로고
    • Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinyl phosphonates
    • (g) Kim, D. Y.; Rhie, D. Y. Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinyl phosphonates. Tetrahedron 1997, 53, 13603-13608;
    • (1997) Tetrahedron , vol.53 , pp. 13603-13608
    • Kim, D.Y.1    Rhie, D.Y.2
  • 36
    • 0642331636 scopus 로고    scopus 로고
    • Reactions of phosphites with nitroalkene derivatives: Syntheses of β-keto phosphonates and α- cyanoalkylphosphonates
    • (h) Kim, D. Y.; Oh, D. Y. Reactions of phosphites with nitroalkene derivatives: Syntheses of β-keto phosphonates and α- cyanoalkylphosphonates. Bull. Korean Chem. Soc. 1997, 18, 994-998.
    • (1997) Bull. Korean Chem. Soc , vol.18 , pp. 994-998
    • Kim, D.Y.1    Oh, D.Y.2
  • 37
    • 0037474646 scopus 로고    scopus 로고
    • Addition of allylindium reagents to acyl phosphonates: Synthesis of tertiary α-hydroxy alkylphosphonates
    • Kim, D. Y.; Wiemer, D. F. Addition of allylindium reagents to acyl phosphonates: Synthesis of tertiary α-hydroxy alkylphosphonates. Tetrahedron Lett. 2003, 44, 2803-2805.
    • (2003) Tetrahedron Lett , vol.44 , pp. 2803-2805
    • Kim, D.Y.1    Wiemer, D.F.2
  • 38
    • 0028818170 scopus 로고
    • Indium mediated coupling of aldehyde with allyl bromides in aqueous media: The issue of region- and diasteroselectivity
    • (a) Isaac, M. B.; Chan, T. H. Indium mediated coupling of aldehyde with allyl bromides in aqueous media: The issue of region- and diasteroselectivity. Tetrahedron Lett. 1995, 36, 8957-8960;
    • (1995) Tetrahedron Lett , vol.36 , pp. 8957-8960
    • Isaac, M.B.1    Chan, T.H.2
  • 39
    • 0034670519 scopus 로고    scopus 로고
    • Organometallic reaction in aqueous media: Indium- and zinc-mediated allylation of sulfonimies
    • (b) Lu, W.; Chan, T. H. Organometallic reaction in aqueous media: Indium- and zinc-mediated allylation of sulfonimies. J. Org. Chem. 2000, 65, 8589-8594.
    • (2000) J. Org. Chem , vol.65 , pp. 8589-8594
    • Lu, W.1    Chan, T.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.