메뉴 건너뛰기




Volumn 10, Issue 3, 2013, Pages 411-424

Synthesis, structure and application of α,β ,-dehydro-α-aminophosphonic and α,β -dehydro-α-aminophosphinic acid derivatives

Author keywords

Asymmetric catalytic hydrogenation; Michaelis Arbuzov reaction; Wadsworth Emmons reaction; aminophosphinic acids; aminophosphonic acids; dehydro aminophosphinates; dehydro aminophosphonates

Indexed keywords


EID: 84901758338     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570179411310030006     Document Type: Article
Times cited : (13)

References (71)
  • 1
    • 17544387855 scopus 로고    scopus 로고
    • Unusual amino acids VIII. Asym­metric hydrogenation of some heteroaiyl-iV-CBZ and VV-BOC aminocinnamic acid derivatives
    • Kreuzfeld, H.J.; Michalik, M.; Döbler, C. Unusual amino acids VIII. Asym­metric hydrogenation of some heteroaiyl-iV-CBZ and VV-BOC aminocinnamic acid derivatives. Amino Acids, 1999,16, 21-27.
    • (1999) Amino Acids , vol.16 , pp. 21-27
    • Kreuzfeld, H.J.1    Michalik, M.2    Döbler, C.3
  • 2
    • 0029857692 scopus 로고    scopus 로고
    • Synthesis of non-proteinogenic (D)-or(L)-amino acids by asymmetric hydrogenation
    • Kreuzfeld, H.J.; Döbler, C.; Schmidt, U.; Krause, H.W. Synthesis of non-proteinogenic (D)-or(L)-amino acids by asymmetric hydrogenation. Amino Acids, 1996,11, 269-282.
    • (1996) Amino Acids , vol.11 , pp. 269-282
    • Kreuzfeld, H.J.1    Döbler, C.2    Schmidt, U.3    Krause, H.W.4
  • 3
    • 56949101063 scopus 로고    scopus 로고
    • An overview of stereoselective synthesis of a-aminophosphonic acids and derivatives
    • Ordonez, M.; Rojas-Cabrera, H.; Cativiela, C. An overview of stereoselective synthesis of a-aminophosphonic acids and derivatives. Tetrahedron, 2009, 65, 17-49.
    • (2009) Tetrahedron , vol.65 , pp. 17-49
    • Ordonez, M.1    Rojas-Cabrera, H.2    Cativiela, C.3
  • 4
    • 33745390196 scopus 로고    scopus 로고
    • α
    • Catalytic asymmetric synthesis of , and ß-amino phosphonic acid derivatives. Chem
    • Ma, J.A. Catalytic asymmetric synthesis of α and ß-amino phosphonic acid derivatives. Chem. Soc. Rev., 2006, 35, 630-636.
    • (2006) Soc. Rev , vol.35 , pp. 630-636
    • Ma, J.A.1
  • 5
    • 84930974679 scopus 로고    scopus 로고
    • One-pot preparation of VV-alkoxycarbonyl-protected acrylate, phosphonate or phosphinate esters com­prises reacting V-acyl-protected esters with dicarbonate ester and then hydra-zine
    • 19,840,861 A1, March
    • Dwars, T.; Schmidt, U.; Krause, H.; Oehme, G. One-pot preparation of VV-alkoxycarbonyl-protected acrylate, phosphonate or phosphinate esters com­prises reacting V-acyl-protected esters with dicarbonate ester and then hydra-zine. DE Patent 19,840,861 A1, March 2, 2000.
    • (2000) DE Patent , pp. 2
    • Dwars, T.1    Schmidt, U.2    Krause, H.3    Oehme, G.4
  • 9
    • 0007193238 scopus 로고    scopus 로고
    • Chemical synthesis of natural product peptides: Coupling methods for the incorporation of noncoded amino acids into peptides
    • Humphrey, J.M.; Chamberlin, A.R. Chemical synthesis of natural product peptides: coupling methods for the incorporation of noncoded amino acids into peptides. Chem. Rev., 1997, 97, 2243-2266.
    • (1997) Chem. Rev , vol.97 , pp. 2243-2266
    • Humphrey, J.M.1    Chamberlin, A.R.2
  • 10
    • 0023872535 scopus 로고
    • Didehydroamino acids (DDAA) and didehydropeptides (DDP)
    • Schmidt, U.; Lieberknecht, A.; Wild, J. Didehydroamino acids (DDAA) and didehydropeptides (DDP). Synthesis, 1988, 159-172.
    • (1988) Synthesis , pp. 159-172
    • Schmidt, U.1    Lieberknecht, A.2    Wild, J.3
  • 11
    • 0040898586 scopus 로고
    • Reaction of diethyl 1-acylamido-2,2-dichlorovinylphosphonates with primary and secondary amines
    • Drach, B.S.; Sviridov, E.P.; Shaturskii, Y.P. Reaction of diethyl 1-acylamido-2,2-dichlorovinylphosphonates with primary and secondary amines. Zh. Obshch. Khim., 1974, 44, 1712-1715.
    • (1974) Zh. Obshch. Khim , vol.44 , pp. 1712-1715
    • Drach, B.S.1    Sviridov, E.P.2    Shaturskii, Y.P.3
  • 12
    • 84863679335 scopus 로고
    • α-Substituted phosphonates. 56. Synthesis and reactions of 1-formylamino-2,2,2-trichloroethanephos phonates
    • Scheidecker, S.; Köckritz, A.; Schnell, M. α-Substituted phosphonates. 56. Synthesis and reactions of 1-formylamino-2,2,2-trichloroethanephos phonates. J. Prakt. Chem., 1990, 332, 968-976.
    • (1990) J. Prakt. Chem , vol.332 , pp. 968-976
    • Scheidecker, S.1    Köckritz, A.2    Schnell, M.3
  • 13
    • 84938328847 scopus 로고
    • α-Substituted phosphonates 68. α-Aminophosphonates and phosphono-substituted heterocycles from diethyl 2,2,2-trichloro-1-isocyanatoethyl]phosphonate. Phosphorus, Sulfur Silicon Relat
    • Köckritz, A.; Schnell, M. α-Substituted phosphonates 68. α-Aminophosphonates and phosphono-substituted heterocycles from diethyl 2,2,2-trichloro-1-isocyanatoethyl]phosphonate. Phosphorus, Sulfur Silicon Relat. Elem., 1993, 83, 125-133.
    • (1993) Elem , vol.83 , pp. 125-133
    • Köckritz, A.1    Schnell, M.2
  • 15
    • 0002014236 scopus 로고
    • New approach to the synthesis of [1-(Acylamino)alkenyl]phosphonic acids, their analogs, and their derivatives
    • Brovarets, V.S.; Zyuz, K.V.; Budnik, L.V.; Solodenko, V.A.; Drach, B.S. New approach to the synthesis of [1-(acylamino)alkenyl]phosphonic acids, their analogs, and their derivatives. Zh. Obshch. Khim., 1993, 63, 1259-1265.
    • (1993) Zh. Obshch. Khim , vol.63 , pp. 1259-1265
    • Brovarets, V.S.1    Zyuz, K.V.2    Budnik, L.V.3    Solodenko, V.A.4    Drach, B.S.5
  • 16
    • 80555123225 scopus 로고
    • Substitution of a carbonyl group by a phosphoryl group in unsaturated azlactones
    • Brovarets, V.S.; Budnik, L.V.; Drach, B.S. Substitution of a carbonyl group by a phosphoryl group in unsaturated azlactones. Zh. Obshch. Khim., 1992, 62, 707-708.
    • (1992) Zh. Obshch. Khim , vol.62 , pp. 707-708
    • Brovarets, V.S.1    Budnik, L.V.2    Drach, B.S.3
  • 17
    • 0030062627 scopus 로고    scopus 로고
    • Catalytic stereoselective synthesis of a-amino phosphonic acid derivatives by asymmetric hydrogenation. Synth
    • Schmidt, U.; Oehme, G.; Krause, H. Catalytic stereoselective synthesis of a-amino phosphonic acid derivatives by asymmetric hydrogenation. Synth. Commun., 1996, 26, 777-781.
    • (1996) Commun , vol.26 , pp. 777-781
    • Schmidt, U.1    Oehme, G.2    Krause, H.3
  • 18
    • 0031683162 scopus 로고    scopus 로고
    • Enantiose-lective synthesis of a-aminophosphonic acid derivatives by hydrogenation
    • Schmidt, U.; Krause, H.W.; Oehme, G.; Michalik, M.; Fischer, C. Enantiose-lective synthesis of a-aminophosphonic acid derivatives by hydrogenation. Chirality, 1998, 10, 564-572.
    • (1998) Chirality , vol.10 , pp. 564-572
    • Schmidt, U.1    Krause, H.W.2    Oehme, G.3    Michalik, M.4    Fischer, C.5
  • 19
    • 0032476780 scopus 로고    scopus 로고
    • Oehme, G. Synthesis of optically active a-aminophosphinic acids by catalytic asymmetric hydrogenation in organic solvents and aqueous mi-cellar media. Angew. Chem. Int
    • Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Fröhlich, R.; Drauz, K.; Oehme, G. Synthesis of optically active a-aminophosphinic acids by catalytic asymmetric hydrogenation in organic solvents and aqueous mi-cellar media. Angew. Chem. Int. Ed., 1998, 37, 2851-2853.
    • Ed., 1998 , vol.37 , pp. 2851-2853
    • Dwars, T.1    Schmidt, U.2    Fischer, C.3    Grassert, I.4    Kempe, R.5    Fröhlich, R.6    Drauz, K.7
  • 20
    • 0001551678 scopus 로고    scopus 로고
    • Synthesis of a-amino phosphonic acids by asymmetric hydrogenation
    • Kitamura, M.; Yoshimura, M.; Tsukamoto, M.; Noyori, R. Synthesis of a-amino phosphonic acids by asymmetric hydrogenation. Enantiomer, 1996, 1, 281-303.
    • (1996) Enantiomer , vol.1 , pp. 281-303
    • Kitamura, M.1    Yoshimura, M.2    Tsukamoto, M.3    Noyori, R.4
  • 21
    • 0008451280 scopus 로고
    • A simple preparation of diethyl 1-acylamino-1-ethenephosphonates
    • Zoh, J. A simple preparation of diethyl 1-acylamino-1-ethenephosphonates. Synthesis, 1981, 324.
    • (1981) Synthesis , pp. 324
    • Zoh, J.1
  • 22
    • 0000634228 scopus 로고    scopus 로고
    • Enantioselective synthesis of a-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation
    • Burk, M.J.; Stammers, T.A.; Straub, J.A. Enantioselective synthesis of a-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation. Org. Lett., 1999,1, 387-390.
    • (1999) Org. Lett , vol.1 , pp. 387-390
    • Burk, M.J.1    Stammers, T.A.2    Straub, J.A.3
  • 25
    • 84985186249 scopus 로고
    • Asymmetric synthesis of α -aminophosphonic acids, I. Enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation of V-[1-(dimethoxyphosphoryl)ethenyl]-formamide
    • Schöllkopf, U.; Hoppe, I.; Thiele, A. Asymmetric synthesis of α -aminophosphonic acids, I. Enantioselective synthesis of L-(1-aminoethyl)phosphonic acid by asymmetric catalytic hydrogenation of V-[1-(dimethoxyphosphoryl)ethenyl]-formamide. Liebigs Ann. Chem., 1985, 555­559.
    • (1985) Liebigs Ann. Chem , pp. 555-559
    • Schöllkopf, U.1    Hoppe, I.2    Thiele, A.3
  • 26
    • 0042572071 scopus 로고
    • Synthesis of α -amino-ß-(4-imidazolyl)ethylphos-phonic acid, the phosphonoisostere of histidine. Chinese
    • Wu, Y.L.; Tishler, M. Synthesis of α -amino-ß-(4-imidazolyl)ethylphos-phonic acid, the phosphonoisostere of histidine. Chinese Chem. Lett., 1991, 2, 95-98.
    • (1991) Chem. Lett , vol.2 , pp. 95-98
    • Wu, Y.L.1    Tishler, M.2
  • 27
    • 0008383548 scopus 로고
    • The synthesis and rotational isomerism of 1-amino-2-imidazol-4-ylethylphosphonic acid [phosphonohistidine, His (P)] and 1-amino-2-imidazol-2-ylethylphosphonic acid [phosphonoisohistidine, Isohis (P)]
    • Merrett, J.H.; Spurden, W.C.; Thomas, W.A.; Tong, B.P.; Whitcombe, I.W.A. The synthesis and rotational isomerism of 1-amino-2-imidazol-4-ylethylphosphonic acid [phosphonohistidine, His (P)] and 1-amino-2-imidazol-2-ylethylphosphonic acid [phosphonoisohistidine, Isohis (P)]. J. Chem. Soc., Perkin Trans. 1, 1988, 61-67.
    • (1988) J. Chem. Soc., Perkin Trans , vol.1 , pp. 61-67
    • Merrett, J.H.1    Spurden, W.C.2    Thomas, W.A.3    Tong, B.P.4    Whitcombe, I.5
  • 28
    • 8444230433 scopus 로고    scopus 로고
    • A concise synthesis of diethyl  -(Tert-butoxycarbonylamino)-1-alkenylphosphonates
    • Blazewska, K.; Gajda, T. A concise synthesis of diethyl  -(tert-butoxycarbonylamino)-1-alkenylphosphonates. Tetrahedron, 2004, 60, 11701-11707.
    • (2004) Tetrahedron , vol.60 , pp. 11701-11707
    • Blazewska, K.1    Gajda, T.2
  • 29
    • 0008241560 scopus 로고
    • Synthesen mit α-metallierten isocyaniden, XXI. Umsetzungen von a-metalliertem isocyanmethan-phosphonsäure-diäthylester mit carbonylverbindungen
    • Schöllkopf, U.; Schröder, R. Synthesen mit α-metallierten isocyaniden, XXI. Umsetzungen von a-metalliertem isocyanmethan-phosphonsäure-diäthylester mit carbonylverbindungen. Tetrahedron Lett., 1973, 14, 633­636.
    • (1973) Tetrahedron Lett , vol.14 , pp. 633-636
    • Schöllkopf, U.1    Schröder, R.2
  • 30
    • 84981440794 scopus 로고
    • Syntheses with a-metalated isocyanides, XXVII. Reactions of a-metalated diethyl isocyanomethyl-and a-isocyanobenzylphosphonates with carbonyl compounds
    • Schöllkopf, U.; Schröder, R.; Stafforst, D. Syntheses with a-metalated isocyanides, XXVII. Reactions of a-metalated diethyl isocyanomethyl-and a-isocyanobenzylphosphonates with carbonyl compounds. Liebigs Ann. Chem., 1974, 44-53.
    • (1974) Liebigs Ann. Chem , pp. 44-53
    • Schöllkopf, U.1    Schröder, R.2    Stafforst, D.3
  • 31
    • 33745728231 scopus 로고    scopus 로고
    • Unexpected four-membered over six-membered ring formation during the synthesis of azaheterocyclic phosphonates: Experimental and theoretical evaluation
    • Van Speybroeck, V.; Moonen, K.; Hemelsoet, K.; Stevens, C.V.; Waroquier, M. Unexpected four-membered over six-membered ring formation during the synthesis of azaheterocyclic phosphonates: experimental and theoretical evaluation. J. Am. Chem. Soc., 2006, 128, 8468-8478.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8468-8478
    • Van Speybroeck, V.1    Moonen, K.2    Hemelsoet, K.3    Stevens, C.V.4    Waroquier, M.5
  • 32
    • 0032509429 scopus 로고    scopus 로고
    • Use of rhodium complexes with amphiphilic and nonamphiphilic ligands for the preparation of chiral a-aminophosphonic acid esters by hydrogenation in micellar media
    • Grassert, I.; Schmidt, U.; Ziegler, S.; Fischer, C.; Oehme, G. Use of rhodium complexes with amphiphilic and nonamphiphilic ligands for the preparation of chiral a-aminophosphonic acid esters by hydrogenation in micellar media. Tetrahedron: Asymmetry, 1998, 9, 4193-4202.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4193-4202
    • Grassert, I.1    Schmidt, U.2    Ziegler, S.3    Fischer, C.4    Oehme, G.5
  • 33
    • 0001296673 scopus 로고    scopus 로고
    • Synthesis of a new class of functionalized chiral bisphospholane ligands and the application in enantioselective hydrogenations
    • Holz, J.; Quirmbach, M.; Schmidt, U.; Heller, D.; Stürmer, R.; Börner, A. Synthesis of a new class of functionalized chiral bisphospholane ligands and the application in enantioselective hydrogenations. J. Org. Chem., 1998, 63, 8031-8034.
    • (1998) J. Org. Chem , vol.63 , pp. 8031-8034
    • Holz, J.1    Quirmbach, M.2    Schmidt, U.3    Heller, D.4    Stürmer, R.5    Börner, A.6
  • 34
    • 0035663852 scopus 로고    scopus 로고
    • Synthesis of  chiral 2,5-bis(Oxymethyl)-functionalized bis(phospholanes) and their application in Rh- and Ru-catalyzed enantiose-lective hydrogenations
    • 0Holz, J.; Stürmer, R.; Schmidt, U.; Drexler, H.J.; Heller, D.; Krimmer, H.P.; Bö rner, A. Synthesis of  chiral 2,5-bis(oxymethyl)-functionalized bis(phospholanes) and their application in Rh- and Ru-catalyzed enantiose-lective hydrogenations. Eur. J. Org. Chem., 2001, 4615-4624.
    • (2001) Eur. J. Org. Chem , pp. 4615-4624
    • 0Holz, J.1    Stürmer, R.2    Schmidt, U.3    Drexler, H.J.4    Heller, D.5    Krimmer, H.P.6    Bö Rner, A.7
  • 35
    • 70350738396 scopus 로고    scopus 로고
    • Asymmetric hydrogenation of enamides, a-enol and α-enamido ester phosphonates catalyzed by IndolPhos-Rh complexes
    • Wassenaar, J.; Reek, J.N.H. Asymmetric hydrogenation of enamides, a-enol and α-enamido ester phosphonates catalyzed by IndolPhos-Rh complexes. J. Org. Chem., 2009, 74, 8403-8406.
    • (2009) J. Org. Chem , vol.74 , pp. 8403-8406
    • Wassenaar, J.1    Reek, J.2
  • 36
    • 77953156495 scopus 로고    scopus 로고
    • Asymmetric hydrogenation with highly active IndolPhos-Rh catalysts: Kinetics and reac­tion mechanism
    • Wassenaar, J.; Kuil, M.; Lutz, M.; Spek, A.L.; Reek, J.N.H. Asymmetric hydrogenation with highly active IndolPhos-Rh catalysts: kinetics and reac­tion mechanism. Chem. Eur. J., 2010, 16, 6509-6517.
    • (2010) Chem. Eur. J , vol.16 , pp. 6509-6517
    • Wassenaar, J.1    Kuil, M.2    Lutz, M.3    Spek, A.L.4    Reek, J.5
  • 37
    • 84930977101 scopus 로고    scopus 로고
    • Fischer, C. Preparation of phosphinic and phosphonic acid derivatives potentially useful as herbicides or as antiviral or antibacterial. DE Patent 19,826,211 A1
    • Schmidt, U.; Dwars, T.; Grassert, I.; Oehme, G.; Fischer, C. Preparation of phosphinic and phosphonic acid derivatives potentially useful as herbicides or as antiviral or antibacterial. DE Patent 19,826,211 A1, December 16, 1999.
    • (1999) December , pp. 16
    • Schmidt, U.1    Dwars, T.2    Grassert, I.3    Oehme, G.4
  • 40
    • 84913150907 scopus 로고
    • Biological activity of aminophosphonic acids. Phosphorus, Sulfur Silicon Relat
    • Kafarski, P.; Lejczak, B. Biological activity of aminophosphonic acids. Phosphorus, Sulfur Silicon Relat. Elem., 1991, 63, 193-215.
    • (1991) Elem , vol.63 , pp. 193-215
    • Kafarski, P.1    Lejczak, B.2
  • 41
    • 0022577081 scopus 로고
    • Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
    • Atherton, F.R.; Hassall, 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    Hassall, C.H.2    Lambert, R.W.3
  • 42
    • 0023034922 scopus 로고
    • Antibacterial activity of phosphono dipeptides related to Alafosfalin
    • Lejczak, B.; Kafarski, P.; Sztajer, H.; Mastalerz, P. Antibacterial activity of phosphono dipeptides related to Alafosfalin. J. Med. Chem., 1986, 29, 2212­2217.
    • (1986) J. Med. Chem , vol.29 , pp. 2212-2217
    • Lejczak, B.1    Kafarski, P.2    Sztajer, H.3    Mastalerz, P.4
  • 43
    • 84985231780 scopus 로고
    • Synthesis, enzyme-substrate interaction, and herbicidal activity of phosphoryl analogues of glycine
    • Natchev, I.A. Synthesis, enzyme-substrate interaction, and herbicidal activity of phosphoryl analogues of glycine. Liebigs Ann. Chem., 1988, 861-867.
    • (1988) Liebigs Ann. Chem , pp. 861-867
    • Natchev, I.A.1
  • 44
    • 84963388098 scopus 로고
    • Synthesis, physical and biological properties of the phosphorus analogues of phenylalanine and related compounds. Phosphorus, Sulfur Silicon Relat
    • Maier, L.; Diel, P.J. Synthesis, physical and biological properties of the phosphorus analogues of phenylalanine and related compounds. Phosphorus, Sulfur Silicon Relat. Elem., 1994, 90, 259-279.
    • (1994) Elem , vol.90 , pp. 259-279
    • Maier, L.1    Diel, P.J.2
  • 45
    • 0038115341 scopus 로고    scopus 로고
    • The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based de­sign, chemistry, and activity
    • Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P. The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based de­sign, chemistry, and activity. J. Med. Chem., 2003, 46, 2641-2655.
    • (2003) J. Med. Chem , vol.46 , pp. 2641-2655
    • Grembecka, J.1    Mucha, A.2    Cierpicki, T.3    Kafarski, P.4
  • 46
    • 0037108173 scopus 로고    scopus 로고
    • Aminophosphonate inhibi­tors of dialkylglycine decarboxylase: Structural basis for slow binding inhibition
    • Liu, W.; Rogers, C.J.; Fisher, A.J.; Toney, M.D. Aminophosphonate inhibi­tors of dialkylglycine decarboxylase: structural basis for slow binding inhibition. Biochemistry, 2002, 41, 12320-12328.
    • (2002) Biochemistry , vol.41 , pp. 12320-12328
    • Liu, W.1    Rogers, C.J.2    Fisher, A.J.3    Toney, M.D.4
  • 47
    • 0034499290 scopus 로고    scopus 로고
    • An overview of recent advances on the synthesis and biological activity of a-aminophosphonic acid derivatives
    • Huang, J.; Chen, R. An overview of recent advances on the synthesis and biological activity of a-aminophosphonic acid derivatives. Heteroat. Chem., 2000, 11, 480-492.
    • (2000) Heteroat. Chem , vol.11 , pp. 480-492
    • Huang, J.1    Chen, R.2
  • 48
    • 0025879040 scopus 로고
    • New a-amino phosphonic acid derivatives of vinblastine: Chemis­try and antitumor activity
    • Lavielle, G.; Hautefaye, P.; Schaeffer, C.; Boutin, J.A.; Cudennec, C.A.; Pierre, A. New a-amino phosphonic acid derivatives of vinblastine: chemis­try and antitumor activity. J. Med. Chem., 1991, 34, 1998-2003.
    • (1991) J. Med. Chem , vol.34 , pp. 1998-2003
    • Lavielle, G.1    Hautefaye, P.2    Schaeffer, C.3    Boutin, J.A.4    Cudennec, C.A.5    Pierre, A.6
  • 49
    • 0024409372 scopus 로고
    • Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond
    • Allen, M.C.; Fuhrer, W.; Tuck, B.; Wade, R.; Wood, J.M. Renin inhibitors. Synthesis of transition-state analogue 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
  • 51
    • 0026801882 scopus 로고
    • New hybrid transition state analog inhibitors of HIV protease with peripheric C2-symmetry
    • Stowasser, B.; Budt, K.-H.; Jian-Qi, L.; Paymen, A.; Ruppert, D. New hybrid transition state analog inhibitors of HIV protease with peripheric C2-symmetry. Tetrahedron Lett., 1992, 33, 6625-6628.
    • (1992) Tetrahedron Lett , vol.33 , pp. 6625-6628
    • Stowasser, B.1    Budt, K.-H.2    Jian-Qi, L.3    Paymen, A.4    Ruppert, D.5
  • 53
    • 84953500772 scopus 로고
    • Asymmetric synthesis of phosphorus analogs of amino acids. Phosphorus, Sulfur Silicon Rela
    •  [53] Kukhar, V.P.; Soloshonok, V.A.; Solodenko, V.A. Asymmetric synthesis of phosphorus analogs of amino acids. Phosphorus, Sulfur Silicon Relat. Elem., 1994, 92, 239-264.
    • (1995) Elem , vol.9 , pp. 239-326
    • Kukhar, V.P.1    Soloshono, V.A.2    Solodenk, V.A.3
  • 54
    • 1842782788 scopus 로고    scopus 로고
    • Asymmetric hydrogenation of α,ß-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: Scope and mechanism of the reaction
    • Gridnev, I.D.; Yasutake, M.; Imamoto, T.; Beletskaya, I.P. Asymmetric hydrogenation of α,ß-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: scope and mechanism of the reaction. Proc. Natl. Acad. Sci. USA, 2004,101, 5385-5390.
    • (2004) Proc. Natl. Acad. Sci. USA , vol.101 , pp. 5385-5390
    • Gridnev, I.D.1    Yasutake, M.2    Imamoto, T.3    Beletskaya, I.P.4
  • 55
    • 41149165906 scopus 로고    scopus 로고
    • Readily available chiral phosphine-aminophosphine ligands for highly efficient Rh-catalyzed asymmetric hydrogenation of a-enol ester phosphonates and a-enamido phosphonates
    • Wang, D.Y.; Huang, J.D.; Hu, X.P.; Deng, J.; Yu, S.B.; Duan, Z.C.; Zheng, Z. Readily available chiral phosphine-aminophosphine ligands for highly efficient Rh-catalyzed asymmetric hydrogenation of a-enol ester phosphonates and a-enamido phosphonates. J. Org. Chem., 2008, 73, 2011-2014.
    • (2008) J. Org. Chem , vol.73 , pp. 2011-2014
    • Wang, D.Y.1    Huang, J.D.2    Hu, X.P.3    Deng, J.4    Yu, S.B.5    Duan, Z.C.6    Zheng, Z.7
  • 56
    • 77954104441 scopus 로고    scopus 로고
    • Impact on hydrogenation catalytic cycle of the R groups' cyclic feature in "R-SMS-Phos"
    • Zupancic, B.; Mohar, B.; Stephan, M. Impact on hydrogenation catalytic cycle of the R groups' cyclic feature in "R-SMS-Phos". Org. Lett., 2010, 12, 3022-2025.
    • (2010) Org. Lett , vol.12 , pp. 2025-3022
    • Zupancic, B.1    Mohar, B.2    Stephan, M.3
  • 57
    • 82455219343 scopus 로고    scopus 로고
    • Asymmetric hydrogenation of α-and ß-enamido phosphonates: Rhodium(I)/monodentate phosphoramidite catalyst. Angew. Chem. Int
    • Zhang, J.; Li, Y.; Wang, Z.; Ding, K. Asymmetric hydrogenation of α-and ß-enamido phosphonates: rhodium(I)/monodentate phosphoramidite catalyst. Angew. Chem. Int. Ed., 2011, 50, 11743-11747.
    • Ed., 2011 , vol.50 , pp. 11743-11747
    • Zhang, J.1    Li, Y.2    Wang, Z.3    Ding, K.4
  • 58
    • 80555149280 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloaddi­tion of diazoalkanes onto dimethyl 1-(Formylamino) ethylenephosphonate: A new route to 1-aminocyclopropanephosphonic acids and 3-phosphorylated pyrazoles
    • Goulioukina, N.S.; Makukhin, N.N.; Beletskaya, I.P. 1,3-Dipolar cycloaddi­tion of diazoalkanes onto dimethyl 1-(formylamino) ethylenephosphonate: a new route to 1-aminocyclopropanephosphonic acids and 3-phosphorylated pyrazoles. Tetrahedron, 2011, 67, 9535-9540.
    • (2011) Tetrahedron , vol.67 , pp. 9535-9540
    • Goulioukina, N.S.1    Makukhin, N.N.2    Beletskaya, I.P.3
  • 59
    • 36849035784 scopus 로고    scopus 로고
    • Natural occurrence, syntheses, and applications of cyclopropyl-group-containing a-amino acids. Part 1. 1-Aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids
    • Brackmann, F.; de Meijere, A. Natural occurrence, syntheses, and applications of cyclopropyl-group-containing a-amino acids. Part 1. 1-Aminocyclopropanecarboxylic acid and other 2,3-methanoamino acids. Chem. Rev., 2007,107, 4493-4537.
    • (2007) Chem. Rev , vol.107 , pp. 4493-4537
    • Brackmann, F.1    De Meijere, A.2
  • 60
    • 0037047532 scopus 로고    scopus 로고
    • Spiro [2.2]pentane as a dissymmetric scaffold for conformationally constrained analogues of glutamic acid: Focus on racemic 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids
    • Pellicciari, R.; Marinozzi, M.; Camaioni, E.; del Carmen Nùnez, M.; Costantino, G.; Gasparini, F.; Giorgi, G.; Macchiarulo, A.; Subramanian, N. Spiro [2.2]pentane as a dissymmetric scaffold for conformationally constrained analogues of glutamic acid: focus on racemic 1-aminospiro[2.2]pentyl-1,4-dicarboxylic acids. J. Org. Chem., 2002, 67, 5497-5507.
    • (2002) J. Org. Chem , vol.67 , pp. 5497-5507
    • Pellicciari, R.1    Marinozzi, M.2    Camaioni, E.3    Del Carmen Nùnez, M.4    Costantino, G.5    Gasparini, F.6    Giorgi, G.7    Macchiarulo, A.8    Subramanian, N.9
  • 61
    • 0023657752 scopus 로고
    • 1-Aminocyclopropanephosphonate: Time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior
    • Erion, M.D.; Walsh, C.T. 1-Aminocyclopropanephosphonate: time-dependent inactivation of 1-aminocyclopropanecarboxylate deaminase and Bacillus stearothermophilus alanine racemase by slow dissociation behavior. Biochemistry, 1987,26, 3417-3425.
    • (1987) Biochemistry , vol.26 , pp. 3417-3425
    • Erion, M.D.1    Walsh, C.T.2
  • 62
    • 64249120244 scopus 로고    scopus 로고
    • Phosphorous acid analogs of novel P2-P4 macrocycles as inhibitors of HCV NS3 protease. Bioorg. Med
    • Pompei, M.; Francesco, M.E.D.; Koch, U.; Liverton, N.J.; Summa, V. Phosphorous acid analogs of novel P2-P4 macrocycles as inhibitors of HCV NS3 protease. Bioorg. Med. Chem. Lett., 2009, 19, 2574-2578.
    • (2009) Chem. Lett , vol.19 , pp. 2574-2578
    • Pompei, M.1    Francesco, M.2    Koch, U.3    Liverton, N.J.4    Summa, V.5
  • 64
    • 34250720448 scopus 로고    scopus 로고
    • Ring transformations of aziridinyl 2-phosphonates: Synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones
    • Vanderhoydonck, B.; Stevens, C.V. Ring transformations of aziridinyl 2-phosphonates: synthesis of 5-phosphono-2-oxazolidinones and 5-phosphono-2-imidazolidinones. Tetrahedron, 2007, 63, 7679-7689.
    • (2007) Tetrahedron , vol.63 , pp. 7679-7689
    • Vanderhoydonck, B.1    Stevens, C.V.2
  • 65
    • 77955858595 scopus 로고    scopus 로고
    • Synthesis of C-heteryl-substituted aminomethylphosphonic acids derivatives. Russ
    • Golovchenko, A.V.; Solomyannyi, R.N.; Brovarets, V.S. Synthesis of C-heteryl-substituted aminomethylphosphonic acids derivatives. Russ. J. Gen. Chem., 2010, 80, 723-727.
    • (2010) J. Gen. Chem , vol.80 , pp. 723-727
    • Golovchenko, A.V.1    Solomyannyi, R.N.2    Brovarets, V.S.3
  • 66
    • 78649326841 scopus 로고    scopus 로고
    • Lead identification of conformationally restricted ß-lactam type com-bretastatin analogues: Synthesis, antiproliferative activity and tubulin targeting effects
    • Carr, M.; Greene, L.M.; Knox, A.J.S.; Lloyd, D.G.; Zisterer, D.M.; Meegan, M.J. Lead identification of conformationally restricted ß-lactam type com-bretastatin analogues: synthesis, antiproliferative activity and tubulin targeting effects. Eur. J. Med. Chem., 2010, 45, 5752-5766.
    • (2010) Eur. J. Med. Chem , vol.45 , pp. 5752-5766
    • Carr, M.1    Greene, L.M.2    Knox, A.3    Lloyd, D.G.4    Zisterer, D.M.5    Meegan, M.J.6
  • 69
    • 84860752761 scopus 로고    scopus 로고
    • Unprecedented transformation of diiron bridging vinyliminium ligands into carboxyamido α and alkylphospho-nate-vinylalkylidenes
    • Marchetti, F.; Zacchini, S.; Zanotti, V. Unprecedented transformation of diiron bridging vinyliminium ligands into carboxyamido α and alkylphospho-nate-vinylalkylidenes. Eur. J. Inorg. Chem., 2012, 2456-2463.
    • (2012) Eur. J. Inorg. Chem , pp. 2456-2463
    • Marchetti, F.1    Zacchini, S.2    Zanotti, V.3
  • 70
    • 63749116332 scopus 로고    scopus 로고
    • Allenylporphyrins: A new motif on the porphyrin periphery
    • Locos, O.B.; Dahms, K.; Senge, M.O. Allenylporphyrins: a new motif on the porphyrin periphery. Tetrahedron Lett., 2009, 50, 2566-2569.
    • (2009) Tetrahedron Lett , vol.50 , pp. 2566-2569
    • Locos, O.B.1    Dahms, K.2    Senge, M.O.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.