Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2002(10): 1613-1616
DOI: 10.1055/s-2002-34234
DOI: 10.1055/s-2002-34234
LETTER
© Georg Thieme Verlag Stuttgart · New York
Metallo-Enzyme Model in Pure Water: Cyclodextrin-Lanthanide Tris(perfluoroalkanesulfonyl)methide and Bis(perfluoroalkanesulfonyl)amide Complexes
Further Information
Received
1 July 2002
Publication Date:
23 September 2002 (online)
Publication History
Publication Date:
23 September 2002 (online)
Abstract
Inclusion complexes of cyclodextrin/cyclodextrin copolymer and lanthanide tris(perfluorobutanesulfonyl)methide/bis(perfluorobutanesulfonyl)amide, namely metallo-enzyme model, are efficient and recyclable super Lewis acid catalysts, which can promote Diels-Alder and Mukaiyama-aldol reactions in pure water.
Key words
cyclodextrin - Lewis acids - catalysis - lanthanides - aqueous reactions
-
1a
Lewis Acids in Organic Synthesis
Yamamoto H. Wiley-VCH; Weinheim: 2000. -
1b
Santelli M.Pons JM. Lewis Acid and Selectivity in Organic Synthesis CRC Press; New York: 1996. -
1c
Selectivities
in Lewis Acid Promoted Reactions
Schinzer D. Kluwer Academic Publishers; Dordrecht: 1988. -
2a
Mikami K.Nakai T. In Kagaku Zokan Vol. 124: Kagaku Dojin; Tokyo: 1995. p.177 -
2b
Mikami K.Terada M.Matsuzawa H. Angew. Chem. Int. Ed. 2002, 41: 5000 - 3
Pugin B.Blaser H.-U. In Comprehensive Asymmetric Catalysis Vol. 3:Jacobsen EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999. p.1367 -
4a
Lubineau A.Auge J. Top. Curr. Chem. 1999, 206: 1 -
4b
Sinou D. Top. Curr. Chem. 1999, 206: 41 -
4c
Cornils B. Top. Curr. Chem. 1999, 206: 133 -
4d
Organic
Reactions in Water
Grieco P. Blackie Academic and Professional; London: 1998. -
4e
Li C.-J.Chan T.-H. Organic Reactions in Aqueous Media Wiley; New York: 1997. -
5a
Bender ML.Komiyama M. Cyclodextrin Chemistry Springer-Verlag; Berlin: 1978. -
5b
Shannon RD. Acta Crystallogr., Sect. A 1976, 32: 751 - 6
Szejtli J. Cyclodextrin and Their Inclusion Complexes Akademiai; Kiado: 1982. - 7
Cyclodextrin
Toda F.Ueno A. Sangyo-Tosho; Tokyo: 1995. -
8a
Comprehensive
Supramolecular Chemistry
Vol. 3:
Szejtli J.Osa T. Pergamon; Oxford: 1996. -
8b
Tsuruta H.Yamaguchi K.Imamoto T. Chem. Commun. 1999, 1703 - 9
Koppel IA.Taft RW.Anvina F.Zhu S.-Z.Hu L.-Q.Sung KS.DesMarteau DD.Yagupolskii LM.Yagupolsukii YL.Kondratenko NV.Volkonskii AY.Vlasov VM.Notario R.Maria P.-C. J. Am. Chem. Soc. 1994, 116: 3047 - 10
Horvath IT.Rabai J. Science 1994, 266: 72 - 11
Gladysz JA. Science 1994, 266: 55 - 12
Curran DP. Angew. Chem. Int. Ed. 1998, 37: 1174 -
13a Sc-
and Yb[N(SO2C4F9)2]3:
Nishikido J.Nakajima H.Saeki T.Ishii A.Mikami K. Synlett 1998, 1347 -
13b
Mikami K.Kotera O.Motoyama Y.Sakaguchi H. Synlett 1996, 171 -
13c Sc- and Yb[C(SO2C8F17)3]3:
Mikami K.Mikami Y.Matsumoto Y.Nishikido J.Yamamoto F.Nakajima H. Tetrahedron Lett. 2001, 42: 289 -
13d Yb[C(SO2C6F13)2SO2C8F17]3:
Barret AGM.Braddock DC.Catterick D.Henshke JP.McKinnell PM. Synlett 2000, 847 - 14 Recently, it was reported that CD
forms inclusion complexes with fluorocarbon surfactants, due to
hydrophobic interaction:
Wilson LD.Verrall RE. J. Phys. Chem. B 1997, 101: 9270 -
15a
Zhang B.Breslow R. J. Am. Chem. Soc. 1997, 119: 1676 -
15b
Otto S.Engberts JBFN.Kwak JCT. J. Am. Chem. Soc. 1998, 120: 9517 -
15c
Tian H.-Y.Chen Y.-J.Wang D.Zeng C.-C.Li C.-J. Tetrahedron Lett. 2000, 41: 2529 -
15d
Manabe K.Mori Y.Wakabayashi T.Nagayama S.Kobayashi S. J. Am. Chem. Soc. 2000, 122: 7202 - 17
Williams DB.Carter CB. Transmission Electron Microscopy Plenum Press; New York: 1996. - 19
Dias LC. J. Braz. Chem. Soc. 1997, 8: 289 - 20
Kagan HB.Riant O. Chem. Rev. 1992, 92: 1007 - 21
Rideout DC.Breslow R. J. Am. Chem. Soc. 1980, 102: 7816 - 22
Breslow R.Guo T. J. Am. Chem. Soc. 1988, 110: 5613 - 23
Nelson SG. Tetrahedron: Asymmetry 1998, 9: 357 - 24
Bach T. Angew. Chem., Int. Ed. Engl. 1994, 33: 417
References
Comm. available from Aldrich Chemical Company, Inc.: Cat. No. 33, 256-9.
18The full percentage of Ln complex/γ-CDP-Ln complex was found to reach only 60% because of the steric repulsion. Indeed, elemental analysis showed that CDP formed a 59% inclusion complex of Ln(C4-methide)3: Calcd Yb, 3.64%. Found: Yb, 3.61%.