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Volumn 5, Issue 11, 1999, Pages 3221-3236

Dendritic TADDOLs: Synthesis, characterization and use in the catalytic enantioselective addition of Et2Zn to benzaldehyde

Author keywords

Alkylations; Asymmetric catalysis; Catalysts; Dendrimers; TADDOLs

Indexed keywords

BENZALDEHYDE; BENZYL DERIVATIVE; DENDRIMER;

EID: 0032704904     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19991105)5:11<3221::AID-CHEM3221>3.0.CO;2-P     Document Type: Article
Times cited : (132)

References (41)
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    • note
    • In ref. [2], Meijer et al. describe the catalysis with different generations of poly(propylene imine) dendrimers which carry chiral amino alcohol moieties on their periphery. Due to interactions between the amino alcohol moieties and due to crowding on the surface of the dendrimers, the selectivities of these catalysts decrease with increasing size of the catalyst. Even though interactions within the catalyst molecules could be decreased by use of a different amino alcohol, the crowding effect still prevented good reaction selectivities.
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    • J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Science 1994, 266, 1226; J. F. G. A. Jansen, H. W. I. Peerlings, E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1995, 107, 1321; Angew. Chem. Int. Ed. Engl. 1995, 34, 1206. With their work on dendritic boxes, Meijer et al. demonstrate a selective inclusion of organic molecules inside a poly(propylene imine) dendrimer with the densely packed surface groups preventing the release of the molecules.
    • (1995) Angew. Chem. , vol.107 , pp. 1321
    • Jansen, J.F.G.A.1    Peerlings, H.W.I.2    De Brabander-Van Den Berg, E.M.M.3    Meijer, E.W.4
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    • J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg, E. W. Meijer, Science 1994, 266, 1226; J. F. G. A. Jansen, H. W. I. Peerlings, E. M. M. de Brabander-van den Berg, E. W. Meijer, Angew. Chem. 1995, 107, 1321; Angew. Chem. Int. Ed. Engl. 1995, 34, 1206. With their work on dendritic boxes, Meijer et al. demonstrate a selective inclusion of organic molecules inside a poly(propylene imine) dendrimer with the densely packed surface groups preventing the release of the molecules.
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    • note
    • In ref. [4], Soai et al. describe the catalysis with ephedrine derivatives attached to poly(amido amine) dendrimers. The selectivity of the catalyzed reaction decreases rapidly with increasing size of the dendrimer used (even in lower generations). The authors explain this effect with interactions between the ephedrine units. It is, however, also possible that the loss of selectivity results from interactions with the polar dendritic branches.
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    • note
    • In ref. [6], Brunner et al. describe very poor selectivities of reactions catalyzed by achiral catalytic sites with chiral dendritic branches. To the best of our knowledge, no other work has yet been published on the influence of dendritic branches on a catalytically active core.
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    • For a first preliminary account see: P. B. Rheiner, H. Sellner, D. Seebach, Helv. Chim. Acta 1997, 80, 2027; P. B. Rheiner, D. Seebach, Polym. Mater. Sci. Eng. 1997, 77, 130.
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    • For a first preliminary account see: P. B. Rheiner, H. Sellner, D. Seebach, Helv. Chim. Acta 1997, 80, 2027; P. B. Rheiner, D. Seebach, Polym. Mater. Sci. Eng. 1997, 77, 130.
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    • note
    • For a dendrimer with peripheral TADDOL units, see ref. [3].
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    • For an investigation of the influence of chiral building blocks on the optical activity of dendritic poly(benzyl ether) branches, see: D. M. Junge, D. V. McGrath, Polym. Mater. Sci. Eng. 1997, 77, 154.
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    • II complexes to catalyze Diels - Alder reactions, Chow et al. also found a big difference in activity when going from the second to the third generation: H.-F. Chow, C. C. Mak, J. Org. Chem. 1997, 62, 5116.
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    • The amounts of the previously mentioned by-products resulting from fivefold coupling were not determined
    • The amounts of the previously mentioned by-products resulting from fivefold coupling were not determined.
  • 39


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.