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Volumn 14, Issue 1, 2012, Pages 1-4

I 2-mediated diversity oriented diastereoselective synthesis of amino acid derived trans-2,5-disubstituted morpholines, piperazines, and thiomorpholines

Author keywords

Amino acids; diastereoselective reaction; morpholines; piperazines; thiomorpholines

Indexed keywords

AMINO ACID; MORPHOLINE DERIVATIVE; PIPERAZINE DERIVATIVE; THIOMORPHOLINE;

EID: 84855603757     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200129t     Document Type: Article
Times cited : (33)

References (30)
  • 1
    • 0037157808 scopus 로고    scopus 로고
    • Syntheses of the sedum and related alkaloids
    • Bates, R.; Sa-Ei, K. Syntheses of the sedum and related alkaloids Tetrahedron 2002, 58, 5957
    • (2002) Tetrahedron , vol.58 , pp. 5957
    • Bates, R.1    Sa-Ei, K.2
  • 3
    • 0033709712 scopus 로고    scopus 로고
    • Stereoselective synthesis of piperidines
    • Laschat, S.; Dickner, T. Stereoselective synthesis of piperidines Synthesis 2000, 1781
    • (2000) Synthesis , pp. 1781
    • Laschat, S.1    Dickner, T.2
  • 4
    • 33646403425 scopus 로고    scopus 로고
    • Strategies for the formation of tetrahydropyran rings in the synthesis of natural products
    • Clarke, P. A.; Santos, S. Strategies for the formation of tetrahydropyran rings in the synthesis of natural products Eur. J. Org. Chem. 2006, 2045-2053
    • (2006) Eur. J. Org. Chem. , pp. 2045-2053
    • Clarke, P.A.1    Santos, S.2
  • 5
    • 39149102146 scopus 로고    scopus 로고
    • Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond-forming reactions
    • Larrosa, I.; Romea, P.; Urpi, F. Synthesis of six-membered oxygenated heterocycles through carbon-oxygen bond-forming reactions Tetrahedron 2008, 64, 2683
    • (2008) Tetrahedron , vol.64 , pp. 2683
    • Larrosa, I.1    Romea, P.2    Urpi, F.3
  • 6
    • 0028203787 scopus 로고
    • 2-symmetric auxiliary. First application in [4 + 2]-cycloadditions leading to 4-oxohexahydropyridazine derivatives
    • 2-symmetric auxiliary. First application in [4 + 2]-cycloadditions leading to 4-oxohexahydropyridazine derivatives Synthesis 1994, 66-72 (Pubitemid 24082772)
    • (1994) Synthesis , Issue.1 , pp. 66-72
    • Enders, D.1    Meyer, O.2    Raabe, G.3    Runsink, J.4
  • 7
    • 0742286917 scopus 로고    scopus 로고
    • Facile Route to 3,5-Disubstituted Morpholines: Enantioselective Synthesis of O-Protected trans-3,5-Bis(hydroxymethyl)morpholines
    • DOI 10.1021/ol035998s
    • Dave, R.; Sasaki, N. A. Facile route to 3,5-disubstituted morpholines: enantioselective synthesis of O-protected trans -3,5-bis(hydroxymethyl) morpholines Org. Lett. 2004, 6, 15-18 (Pubitemid 38160979)
    • (2004) Organic Letters , vol.6 , Issue.1 , pp. 15-18
    • Dave, R.1    Andre Sasaki, N.2
  • 8
    • 1642293910 scopus 로고    scopus 로고
    • The Selective Norepinephrine Reuptake Inhibitor Antidepressant Reboxetine: Pharmacological and Clinical Profile
    • Hajos, M.; Fleishaker, J. C.; Filipiak-Reisner, J. K.; Brown, M. T.; Wong, E. H. F. The selective norepinephrine reuptake inhibitor antidepressant reboxetine: pharmacological and clinical profile CNS Drug Rev. 2004, 10, 23-44 (Pubitemid 38381173)
    • (2004) CNS Drug Reviews , vol.10 , Issue.1 , pp. 23-44
    • Hajos, M.1    Fleishaker, J.C.2    Filipiak-Reisner, J.K.3    Brown, M.T.4    Wong, E.H.F.5
  • 9
    • 0004157834 scopus 로고
    • Simultaneous determination of fenpropimorph and the corresponding metabolite fenpropimorphic acid in soil
    • Dieckmann, H.; Stockmaier, M.; Kreuzig, R.; Bahadir, M. Simultaneous determination of fenpropimorph and the corresponding metabolite fenpropimorphic acid in soil Fresenius' J. Anal. Chem. 1993, 345, 784
    • (1993) Fresenius' J. Anal. Chem. , vol.345 , pp. 784
    • Dieckmann, H.1    Stockmaier, M.2    Kreuzig, R.3    Bahadir, M.4
  • 10
    • 33749678965 scopus 로고    scopus 로고
    • Preparation of anti-pefloxacin antibody and development of an indirect competitive enzyme-linked immunosorbent assay for detection of pefloxacin residue in chicken liver
    • DOI 10.1021/jf061309q
    • Lu, S.; Zhang, Y.; Liu, J.; Zhao, C.; Liu, W.; Xi, R. Preparation of anti-pefloxacin antibody and development of an indirect competitive enzyme-linked immunosorbent assay for detection of pefloxacin residue in chicken liver J. Agric. Food. Chem. 2006, 54, 6995-7000 (Pubitemid 44554913)
    • (2006) Journal of Agricultural and Food Chemistry , vol.54 , Issue.19 , pp. 6995-7000
    • Lu, S.1    Zhang, Y.2    Liu, J.3    Zhao, C.4    Liu, W.5    Xi, R.6
  • 11
    • 29144441068 scopus 로고    scopus 로고
    • 3 receptor agents with N-[4-(4-Arylpiperazin-1-yl)butyl]-arylcarboxamide structure
    • DOI 10.1021/jm050729o
    • Leopoldo, M.; Lacitiva, E.; Colabufo, N. A.; Contino, M.; Berardi, F.; Perrone, R. First structure-activity relationship study on dopamine D3 receptor agents with N -[4-(4-arylpiperazin-1-yl)butyl]carboxamide structure J. Med. Chem. 2005, 48, 7919-7922 (Pubitemid 41798423)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.25 , pp. 7919-7922
    • Leopoldo, M.1    Lacivita, E.2    Colabufo, N.A.3    Contino, M.4    Berardi, F.5    Perrone, R.6
  • 12
    • 0028147531 scopus 로고
    • Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524
    • DOI 10.1016/S0040-4039(00)75787-X
    • Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Welss, K. M.; Volante, R. P.; Reider, P. J. Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524 Tetrahedron Lett. 1994, 35, 673-676 (Pubitemid 24067961)
    • (1994) Tetrahedron Letters , vol.35 , Issue.5 , pp. 673-676
    • Askin, D.1    Eng, K.K.2    Rossen, K.3    Purick, R.M.4    Wells, K.M.5    Volante, R.P.6    Reider, P.J.7
  • 14
    • 0028791862 scopus 로고
    • Syntheses, structures, and enzymic evaluations of conformationally constrained, analog inhibitors of carnitine acetyltransferase: (2 R,6 R)-, (2 S,6 S)-, (2 R,6 S)-, and (2 S,6 R)-6-(carboxylatomethyl)-2-(hydroxymethyl)-2,4, 4-trimethylmorpholinium
    • Sun, G.; Savle, P. S.; Gandour, R. D.; Bhaírd, N. N. a; Ramsay, R. R.; Fronczek, F. R. Syntheses, structures, and enzymic evaluations of conformationally constrained, analog inhibitors of carnitine acetyltransferase: (2 R,6 R)-, (2 S,6 S)-, (2 R,6 S)-, and (2 S,6 R)-6-(carboxylatomethyl)-2- (hydroxymethyl)-2,4,4-trimethylmorpholinium J. Org. Chem. 1995, 60, 6688-6695
    • (1995) J. Org. Chem. , vol.60 , pp. 6688-6695
    • Sun, G.1    Savle, P.S.2    Gandour, R.D.3    Bhaírd, N.N.A.4    Ramsay, R.R.5    Fronczek, F.R.6
  • 19
    • 45549086270 scopus 로고    scopus 로고
    • An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulphonium salts
    • Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulphonium salts Angew. Chem., Int. Ed. 2008, 47, 3784-3786
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3784-3786
    • Yar, M.1    McGarrigle, E.M.2    Aggarwal, V.K.3
  • 20
    • 8444232793 scopus 로고    scopus 로고
    • Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions
    • DOI 10.1016/j.tet.2004.10.008, PII S0040402004016886
    • Lupi, V.; Albanese, D.; Landini, D.; Scaletti, D.; Penso, M. Synthesis of 2,6-disubstituted morpholines through regioselective oxirane ring opening by tosylamide under PTC conditions Tetrahedron 2004, 60, 11709-11718 (Pubitemid 39487418)
    • (2004) Tetrahedron , vol.60 , Issue.51 , pp. 11709-11718
    • Lupi, V.1    Albanese, D.2    Landini, D.3    Scaletti, D.4    Penso, M.5
  • 21
    • 1642486447 scopus 로고    scopus 로고
    • Efficient, stereoselective synthesis of trans-2,5-disubstituted morpholines
    • DOI 10.1021/ol049861t
    • Lanman, B. A.; Myers, A. G. Efficient, stereoselective synthesis of trans -2,5-disubstituted morpholines Org. Lett. 2004, 6, 1045-1047 (Pubitemid 38404300)
    • (2004) Organic Letters , vol.6 , Issue.6 , pp. 1045-1047
    • Lanman, B.A.1    Myers, A.G.2
  • 22
    • 67650351948 scopus 로고    scopus 로고
    • New strategy for the synthesis of substituted morpholine
    • Leathen, M. L.; Rosen, B. R.; Wolfe, J. P. New strategy for the synthesis of substituted morpholine J. Org. Chem. 2009, 74, 5107-5110
    • (2009) J. Org. Chem. , vol.74 , pp. 5107-5110
    • Leathen, M.L.1    Rosen, B.R.2    Wolfe, J.P.3
  • 23
    • 0037156593 scopus 로고    scopus 로고
    • Recent advances in the synthesis of diketopiperazins
    • Dinsmore, C. J.; Beshore, D. C. Recent advances in the synthesis of diketopiperazins Tetrahedron 2002, 58, 3297-3312
    • (2002) Tetrahedron , vol.58 , pp. 3297-3312
    • Dinsmore, C.J.1    Beshore, D.C.2
  • 24
    • 34047239151 scopus 로고    scopus 로고
    • Diversity-oriented synthetic approach to naturally abundant s-amino acids based benzannulated enantiomerically pure medium ring heterocyclic scaffolds employing inter- and intramolecular mitsunobu reactions
    • Mishra, J. K.; Panda, G. Diversity-oriented synthetic approach to naturally abundant s-amino acids based benzannulated enantiomerically pure medium ring heterocyclic scaffolds employing inter- and intramolecular mitsunobu reactions J. Comb. Chem. 2007, 9, 321
    • (2007) J. Comb. Chem. , vol.9 , pp. 321
    • Mishra, J.K.1    Panda, G.2
  • 26
    • 72049122105 scopus 로고    scopus 로고
    • Amino acid based enantiomerically pure 3-substituted benzofused heterocycles: A new class of antithrombotic agents
    • Mishra, J. K.; Samanta, K.; Jain, M.; Dikshit, M.; Panda, G. Amino acid based enantiomerically pure 3-substituted benzofused heterocycles: a new class of antithrombotic agents Bioorg. Med. Chem. Lett. 2010, 20, 244
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 244
    • Mishra, J.K.1    Samanta, K.2    Jain, M.3    Dikshit, M.4    Panda, G.5
  • 27
    • 78650796304 scopus 로고    scopus 로고
    • Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis -2,5-disubstituted chiral piperazines
    • Samanta, K.; Panda, G. Regioselective ring-opening of amino acid-derived chiral aziridines: an easy access to cis -2,5-disubstituted chiral piperazines Chem.-Asian J. 2011, 189-197
    • (2011) Chem.-Asian J. , pp. 189-197
    • Samanta, K.1    Panda, G.2
  • 28
    • 0042766849 scopus 로고    scopus 로고
    • Diastereoselective synthesis of piperazines by Manganese-mediated reductive cyclization
    • Mercer, G. J.; Sigman, M. S. Diastereoselective synthesis of piperazines by Manganese-mediated reductive cyclization Org. Lett. 2003, 5, 1591
    • (2003) Org. Lett. , vol.5 , pp. 1591
    • Mercer, G.J.1    Sigman, M.S.2
  • 29
    • 33748274686 scopus 로고    scopus 로고
    • Synthesis of 3,5-disubstituted piperazinones via palladium(II)-catalyzed amination
    • DOI 10.1055/s-2006-948208
    • Ferber, B.; Prestat, G.; Vogel, S.; Madec, D.; Poli, G. Synthesis of 3,5-disubstituted piperazinones via palladium(II)-catalyzed amination Synlett 2006, 2133-2135 (Pubitemid 44318234)
    • (2006) Synlett , Issue.13 , pp. 2133-2135
    • Ferber, B.1    Prestat, G.2    Vogel, S.3    Madec, D.4    Poli, G.5
  • 30
    • 33644535452 scopus 로고    scopus 로고
    • Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines
    • references cited therein.
    • Viso, A.; Fernandez de la Pradilla, R.; Flores, A.; Garcia, A.; Tortosa, M.; Lopez-Rodriguez, M. L. Synthesis of highly substituted enantiopure piperazines and ketopiperazines from vicinal N-sulfinyl diamines J. Org. Chem. 2006, 71, 1442 and references cited therein.
    • (2006) J. Org. Chem. , vol.71 , pp. 1442
    • Viso, A.1    Fernandez De La Pradilla, R.2    Flores, A.3    Garcia, A.4    Tortosa, M.5    Lopez-Rodriguez, M.L.6


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