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Volumn 6, Issue 20, 2000, Pages 3692-3705

Immobilization of BINOL by cross-linking copolymerization of styryl derivatives with styrene, and applications in enantioselective Ti and Al Lewis acid mediated additions of Et2Zn and Me3SiCN to aldehydes and of diphenyl nitrone to enol ethers

Author keywords

1,1 binaphthols; Asymmetric catalysis; Catalysts; Dendritic cross linkers; Polymers

Indexed keywords

ALDEHYDE; ALUMINUM; ETHER DERIVATIVE; NAPHTHOL DERIVATIVE; NITRONE DERIVATIVE; SILICON DERIVATIVE; STYRENE DERIVATIVE; TITANIUM; ZINC DERIVATIVE;

EID: 0034675670     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20001016)6:20<3692::AID-CHEM3692>3.0.CO;2-0     Document Type: Article
Times cited : (122)

References (75)
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    • This compound was extremely sensitive to both air and light, and was therefore directly employed in subsequent coupling steps without prior storage
    • This compound was extremely sensitive to both air and light, and was therefore directly employed in subsequent coupling steps without prior storage.
  • 54
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    • Special precautions had to be taken to avoid undesired polymerization of the styryl-substituted compounds during synthesis and workup. Only sufficiently dilute solutions were heated; crude products were purified immediately by flash-column chromatography; purified compounds were stored in a refrigerator, with exclusion of light
    • Special precautions had to be taken to avoid undesired polymerization of the styryl-substituted compounds during synthesis and workup. Only sufficiently dilute solutions were heated; crude products were purified immediately by flash-column chromatography; purified compounds were stored in a refrigerator, with exclusion of light.
  • 56
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    • We also tried to synthesize a para-substituted spacer molecule by etherification of 4-hydroxy-benzyl alcohol and 4-vinyl-benzyl chloride, followed by Appel reaction. However, the resulting benzyl bromide could not be isolated due to hydrolysis during workup
    • We also tried to synthesize a para-substituted spacer molecule by etherification of 4-hydroxy-benzyl alcohol and 4-vinyl-benzyl chloride, followed by Appel reaction. However, the resulting benzyl bromide could not be isolated due to hydrolysis during workup.
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    • 3 as base and acetone as solvent did not suppress silyl migration and gave the coupling products in comparable yields after heating for 72 h at 50-60°C. In order to reduce the risk of racemization of BINOL during the several days of coupling conditions at elevated temperatures, we decided to perform the coupling step under the conditions described above (NaH, DMF, RT)
    • 3 as base and acetone as solvent did not suppress silyl migration and gave the coupling products in comparable yields after heating for 72 h at 50-60°C. In order to reduce the risk of racemization of BINOL during the several days of coupling conditions at elevated temperatures, we decided to perform the coupling step under the conditions described above (NaH, DMF, RT).
  • 61
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    • Cross-linker 13 could not be successfully deprotected. The reaction product of the deprotection reaction was insoluble in every solvent tested, so that no characterization was possible
    • Cross-linker 13 could not be successfully deprotected. The reaction product of the deprotection reaction was insoluble in every solvent tested, so that no characterization was possible.
  • 67
    • 85037454242 scopus 로고    scopus 로고
    • A similar observation was made by Yoshida et al. (ref. [24]) by using dendritically substituted BINOLs (with Fréchet branches without peripheral styryl groups up to the third generation) in the Ti-BINOLate-mediated addition of allyl stannane to PhCHO
    • A similar observation was made by Yoshida et al. (ref. [24]) by using dendritically substituted BINOLs (with Fréchet branches without peripheral styryl groups up to the third generation) in the Ti-BINOLate-mediated addition of allyl stannane to PhCHO.
  • 69
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    • 2Zn to PhCHO; most probably the BINOL moiety had racemized during the copolymerization process
    • 2Zn to PhCHO; most probably the BINOL moiety had racemized during the copolymerization process.
  • 70
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    • 2O was added. In this way, the salts could be completely removed from the beads
    • 2O was added. In this way, the salts could be completely removed from the beads.
  • 71
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    • The same trend was also observed during our work on polymer-bound cross-linking TADDOLs (ref. [17])
    • The same trend was also observed during our work on polymer-bound cross-linking TADDOLs (ref. [17]).
  • 74
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    • 4 might still have been present within the polymer beads, giving rise to formation of racemic cyanohydrine
    • 4 might still have been present within the polymer beads, giving rise to formation of racemic cyanohydrine.
  • 75
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    • Note added in proof: After submission of this paper, a publication appeared in which grafting of a BINOL to Merrifield resin through a 3,3′-dicarboxylic acid amide was described: X.-W. Yang, J.-H. Sheng, C.-S. Da, H.-S. Wang, W. Su, R. Wang, A. S. C. Chan, J. Org. Chem. 2000, 65, 295-296.
    • (2000) J. Org. Chem. , vol.65 , pp. 295-296
    • Yang, X.-W.1    Sheng, J.-H.2    Da, C.-S.3    Wang, H.-S.4    Su, W.5    Wang, R.6    Chan, A.S.C.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.