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Volumn 11, Issue 10, 1999, Pages 745-751

Catalytic asymmetric dihydroxylation of alkenes induced by polymeric chiral ligands

Author keywords

Asymmetric synthesis; Chiral polymers; Cinchona alkaloids derivatives; Heterogeneous catalysis; Optically active diols

Indexed keywords

ALKENE; LIGAND;

EID: 0032731807     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:10<745::AID-CHIR2>3.0.CO;2-W     Document Type: Article
Times cited : (18)

References (31)
  • 1
    • 0000067960 scopus 로고    scopus 로고
    • Catalytic asymmetric dihydroxylation
    • Ojima I, editor. New York: VCH Publishers
    • (a) Johnson RA, Sharpless KB. Catalytic asymmetric dihydroxylation. In: Ojima I, editor. Catalytic asymmetric synthesis. New York: VCH Publishers; 1998. p 227-272.
    • (1998) Catalytic Asymmetric Synthesis , pp. 227-272
    • Johnson, R.A.1    Sharpless, K.B.2
  • 2
    • 0026469610 scopus 로고
    • Recent advances in the asymmetric dihydroxylation of alkenes
    • (b) Lohray BB. Recent advances in the asymmetric dihydroxylation of alkenes. Tetrahedron: Asymmetry 1992;3:1317-1349.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1317-1349
    • Lohray, B.B.1
  • 4
    • 0030760142 scopus 로고    scopus 로고
    • In defence of the catalytic asymmetric cis dihydroxylation of olefins utilizing insoluble polymeric ligands
    • Salvadori P, Pini D, Petri A. In defence of the catalytic asymmetric cis dihydroxylation of olefins utilizing insoluble polymeric ligands. J Am Chem Soc 1997;119:6929-6930.
    • (1997) J Am Chem Soc , vol.119 , pp. 6929-6930
    • Salvadori, P.1    Pini, D.2    Petri, A.3
  • 6
    • 84920356186 scopus 로고    scopus 로고
    • Tesi di Laurea. Università di Pisa, Italy; 1990
    • (b) Petri A. Tesi di Laurea. Università di Pisa, Italy; 1990.
    • Petri, A.1
  • 8
    • 0025286788 scopus 로고
    • Heterogeneous catalytic asymmetric dihydroxylation: Use of a polymer-bound alkaloid
    • Kim BM, Sharpless KB. Heterogeneous catalytic asymmetric dihydroxylation: use of a polymer-bound alkaloid. Tetrahedron Lett 1990; 31:3003-3006.
    • (1990) Tetrahedron Lett , vol.31 , pp. 3003-3006
    • Kim, B.M.1    Sharpless, K.B.2
  • 9
    • 0027441839 scopus 로고
    • A new crosslinked polymer for the heterogeneous catalytic asymmetric dihydroxylation of alkenes
    • Pini D, Petri A, Salvadori P. A new crosslinked polymer for the heterogeneous catalytic asymmetric dihydroxylation of alkenes. Tetrahedron: Asymmetry 1993;4:2351-2354.
    • (1993) Tetrahedron: Asymmetry , vol.4 , pp. 2351-2354
    • Pini, D.1    Petri, A.2    Salvadori, P.3
  • 10
    • 0027985013 scopus 로고
    • Heterogeneous catalytic asymmetric dihydroxylation of olefins: A new polymeric support and a process improvement
    • Pini D, Petri A, Salvadori P. Heterogeneous catalytic asymmetric dihydroxylation of olefins: a new polymeric support and a process improvement. Tetrahedron 1994;50:11321-11328.
    • (1994) Tetrahedron , vol.50 , pp. 11321-11328
    • Pini, D.1    Petri, A.2    Salvadori, P.3
  • 11
    • 0029608832 scopus 로고
    • Synthesis of optically active diols by using an efficient polymer bound Cinchona alkaloid derivative
    • Petri A, Pini D, Rapaccini S, Salvadori P. Synthesis of optically active diols by using an efficient polymer bound Cinchona alkaloid derivative. Chirality 1995;7:580-585.
    • (1995) Chirality , vol.7 , pp. 580-585
    • Petri, A.1    Pini, D.2    Rapaccini, S.3    Salvadori, P.4
  • 12
    • 0028918073 scopus 로고
    • Heterogeneous enantioselective dihydroxylation of aliphatic olefins: A comparison between different polymeric Cinchona alkaloids derivatives
    • Petri A, Pini D, Salvadori P. Heterogeneous enantioselective dihydroxylation of aliphatic olefins: a comparison between different polymeric Cinchona alkaloids derivatives. Tetrahedron Lett 1995;36:1549-1552.
    • (1995) Tetrahedron Lett , vol.36 , pp. 1549-1552
    • Petri, A.1    Pini, D.2    Salvadori, P.3
  • 13
    • 0026675947 scopus 로고
    • Asymmetric catalytic dihydroxylation of alkenes on polymer support: Scope and limitation
    • Lohray BB, Thomas A, Chittari P, Ahuja JR, Dhal PK. Asymmetric catalytic dihydroxylation of alkenes on polymer support: scope and limitation. Tetrahedron Lett 1992;33:5453-5456.
    • (1992) Tetrahedron Lett , vol.33 , pp. 5453-5456
    • Lohray, B.B.1    Thomas, A.2    Chittari, P.3    Ahuja, J.R.4    Dhal, P.K.5
  • 14
    • 0027938920 scopus 로고
    • Unprecedented reactivity and selectivity in heterogeneous asymmetric catalytic dihydroxylation of alkenes
    • Lohray BB, Nandanan E, Bhushan V. Unprecedented reactivity and selectivity in heterogeneous asymmetric catalytic dihydroxylation of alkenes. Tetrahedron Lett 1994;35:6559-6562.
    • (1994) Tetrahedron Lett , vol.35 , pp. 6559-6562
    • Lohray, B.B.1    Nandanan, E.2    Bhushan, V.3
  • 15
    • 0028880555 scopus 로고
    • Polymeric Cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins: The influence of the polymer backbone polarity on the compatibility between polymer support and reaction medium
    • Song CE, Roh EJ, Lee S, Kim IO. Polymeric Cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins: the influence of the polymer backbone polarity on the compatibility between polymer support and reaction medium. Tetrahedron: Asymmetry 1995; 6:2687-2694.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 2687-2694
    • Song, C.E.1    Roh, E.J.2    Lee, S.3    Kim, I.O.4
  • 16
    • 0029883631 scopus 로고    scopus 로고
    • Efficient and practical polymeric catalysts for heterogeneous asymmetric dihydroxylation of olefins
    • Song CE, Yang JW, Ha HJ, Lee S. Efficient and practical polymeric catalysts for heterogeneous asymmetric dihydroxylation of olefins. Tetrahedron: Asymmetry 1996;7:645-648.
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 645-648
    • Song, C.E.1    Yang, J.W.2    Ha, H.J.3    Lee, S.4
  • 17
    • 0030956225 scopus 로고    scopus 로고
    • New polymer supported cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins
    • Nandanan E, Sudalai A, Ravindranathan T. New polymer supported Cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins. Tetrahedron Lett 1997;38:2577-2580.
    • (1997) Tetrahedron Lett , vol.38 , pp. 2577-2580
    • Nandanan, E.1    Sudalai, A.2    Ravindranathan, T.3
  • 19
    • 0024700330 scopus 로고
    • Protection and polymerization of functional monomers. 13. Anionic living polymerization of tert-butyl 4-vinylbenzoate
    • Ishizone T, Hirao A, Nakahama S. Protection and polymerization of functional monomers. 13. Anionic living polymerization of tert-butyl 4-vinylbenzoate. Macromolecules 1989;22:2895-2901.
    • (1989) Macromolecules , vol.22 , pp. 2895-2901
    • Ishizone, T.1    Hirao, A.2    Nakahama, S.3
  • 20
    • 19744377612 scopus 로고    scopus 로고
    • Preparation, structure and morphology of polymer supports
    • (a) Sherrington DC. Preparation, structure and morphology of polymer supports. Chem Commun 1998;2275-2286.
    • (1998) Chem Commun , pp. 2275-2286
    • Sherrington, D.C.1
  • 21
    • 0030777553 scopus 로고    scopus 로고
    • Functionalised polymers: Recent developments and new applications in synthetic organic chemistry
    • (b) Shuttleworth SJ, Allin SM, Sharma PK. Functionalised polymers: recent developments and new applications in synthetic organic chemistry. Synthesis 1997;1217-1239.
    • (1997) Synthesis , pp. 1217-1239
    • Shuttleworth, S.J.1    Allin, S.M.2    Sharma, P.K.3
  • 22
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. I. The synthesis of a tetrapeptide
    • Merrifield RB. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J Am Chem Soc 1963;85:2149-2154.
    • (1963) J Am Chem Soc , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 23
    • 0018922392 scopus 로고
    • Functional polymers. II. Synthesis and properties of new polymeric Cinchona alkaloids
    • Kobayashi N, Iwai K. Functional polymers. II. Synthesis and properties of new polymeric Cinchona alkaloids. J Polym Sci Polym Chem Ed 1980;18:223-233.
    • (1980) J Polym Sci Polym Chem Ed , vol.18 , pp. 223-233
    • Kobayashi, N.1    Iwai, K.2
  • 24
    • 0001730768 scopus 로고
    • Transition metal catalyzed organic syntheses via polymer-attached optically active phosphine ligands. Synthesis of r aminoacids and hydratropic acid by hydrogenation
    • Takaishi N, Imai H, Bertelo CA Stille JK. Transition metal catalyzed organic syntheses via polymer-attached optically active phosphine ligands. Synthesis of R aminoacids and hydratropic acid by hydrogenation. J Am Chem Soc 1978;100:264-268.
    • (1978) J Am Chem Soc , vol.100 , pp. 264-268
    • Takaishi, N.1    Imai, H.2    Bertelo, C.A.3    Stille, J.K.4
  • 25
    • 84920346770 scopus 로고    scopus 로고
    • note
    • It should be noted that the washings of all polymers were examined by UV spectrophotometric analysis to ensure that the monomer was covalently bonded and not merely absorbed in the swelled polymer.
  • 27
    • 0025285540 scopus 로고
    • Preclusion of the "second cycle" in the osmium-catalyzed asymmetric dihydroxylation of olefins leads to a superior process
    • (b) Kwong H, Sorato C, Ogino Y, Chen H, Sharpless KB. Preclusion of the "second cycle" in the osmium-catalyzed asymmetric dihydroxylation of olefins leads to a superior process. Tetrahedron Lett 1990; 31:2999-3002.
    • (1990) Tetrahedron Lett , vol.31 , pp. 2999-3002
    • Kwong, H.1    Sorato, C.2    Ogino, Y.3    Chen, H.4    Sharpless, K.B.5
  • 30
    • 84920345887 scopus 로고    scopus 로고
    • note
    • In our previous work, we had adopted the standard time corresponding to a homogeneous reaction (Ref. 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.