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Volumn 7, Issue 13, 2001, Pages 2873-2887

Preparation of dendritic and non-dendritic styryl-substituted Salens for cross-linking suspension copolymerization with styrene and multiple use of the corresponding Mn and Cr complexes in enantioselective epoxidations and Hetero-Diels - Alder reactions

Author keywords

Asymmetric catalysis; Cycloadditions; Dendritic cross linkers; Epoxidations; Polymer bound Salen

Indexed keywords

ACETYLENE; ALDEHYDES; BROMINE; CATALYSTS; COMPLEXATION; CONDENSATION; COPOLYMERIZATION; POLYSTYRENES; STYRENE;

EID: 0035796531     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010702)7:13<2873::AID-CHEM2873>3.0.CO;2-C     Document Type: Article
Times cited : (113)

References (87)
  • 6
    • 0033520298 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 2476-2514.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2476-2514
  • 14
    • 0000775513 scopus 로고    scopus 로고
    • (Eds.: B. K. Hodnett, A. P. Kybett, J. H. Clark, K. Smith), The Royal Society of Chemistry
    • H.-U. Blaser, B. Pugin in Supported Reagents and Catalysts in Chemistry (Eds.: B. K. Hodnett, A. P. Kybett, J. H. Clark, K. Smith), The Royal Society of Chemistry, 1998, pp. 101-109.
    • (1998) Supported Reagents and Catalysts in Chemistry , pp. 101-109
    • Blaser, H.-U.1    Pugin, B.2
  • 19
    • 0032538773 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1998, 37, 2922-2959.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 2922-2959
  • 23
    • 0003191934 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 92-138, and references therein.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 92-138
  • 30
    • 0034678774 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 1503-1506.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1503-1506
  • 31
    • 0001615908 scopus 로고    scopus 로고
    • TADDOL has recently also successfully been immobilized on silica by grafting: A. Heckel, D. Seebach, Angew. Chem. 2000, 112, 165-167;
    • (2000) Angew. Chem. , vol.112 , pp. 165-167
    • Heckel, A.1    Seebach, D.2
  • 37
    • 0033549504 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38, 1918-1920.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1918-1920
  • 39
  • 40
    • 0028873867 scopus 로고
    • Angew. Chem. Int. Ed. Engl. 1995, 34, 1812-1832, and references therein.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1812-1832
  • 41
    • 0002784283 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P.J. Stang), Wiley-VCH, Weinheim
    • G. Wulff in Templated Organic Synthesis (Eds.: F. Diederich, P.J. Stang), Wiley-VCH, Weinheim, 2000, pp. 39-73, and references therein.
    • (2000) Templated Organic Synthesis , pp. 39-73
    • Wulff, G.1
  • 43
  • 71
    • 0001405437 scopus 로고
    • (Eds.: E. W. Abel, F. G. A. Stone, E. Wilkinson), Pergamon, New York
    • b) E. N. Jacobsen in Comprehensive Organometallic Chemistry II (Eds.: E. W. Abel, F. G. A. Stone, E. Wilkinson), Pergamon, New York, 1995, pp. 1097-1135;
    • (1995) Comprehensive Organometallic Chemistry II , pp. 1097-1135
    • Jacobsen, E.N.1
  • 76
    • 18844427917 scopus 로고    scopus 로고
    • note
    • We also tried to synthesize 11 in an "inverse" way by first attaching a phenyl-acetylene moiety to 4b, followed by coupling of the resulting dendritic acetylene branch to 3-tert-butyl-5-bromo salicylic aldehyde by Sonogashira coupling. Unfortunately, mainly homo-coupling of the dendritic acetylene moieties occurred under the coupling conditions, with 11 being formed in only minor amounts.
  • 77
    • 18844399719 scopus 로고    scopus 로고
    • note
    • In solution generally less than 5 mol% of Mn-Salen are used for the epoxidation reactions. We decided to use 20 mol% of catalyst both for homogeneous and heterogeneous reactions. With the heterogeneous catalysts being recyclable many times, the amount of catalyst employed is not as crucial as under homogeneous conditions!
  • 82
    • 18844370727 scopus 로고    scopus 로고
    • note
    • In most literature examples, polymer-bound Mn-Salens have been prepared by copolymerization or grafting of a suitable pre-formed Mn-Salen. References [28b] and [31] are examples for loading a polymer-bound Salen with manganese after copolymerization. In contrast to the procedures described in [28b] and [31], we had to use DMF as co-solvent, because our beads do not swell in pure EtOH.
  • 83
    • 85046910392 scopus 로고    scopus 로고
    • note
    • 2O were added, and the organic phase was subjected to CGC analysis.
  • 84
    • 84856549574 scopus 로고    scopus 로고
    • A very recent review: K. A. Jørgensen, Angew. Chem. 2000, 112, 3702-3733;
    • (2000) Angew. Chem. , vol.112 , pp. 3702-3733
    • Jørgensen, K.A.1
  • 85
    • 0034675619 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2000, 39, 3558-3588, and references therein.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3558-3588
  • 87
    • 18844388794 scopus 로고    scopus 로고
    • note
    • For determination of the enantioselectivities under homogeneous conditions we used a Salen prepared by condensation of (R,R)-cyclohexane diamine and 3-tert-butyl-5-bromo salicylic aldehyde.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.