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Synlett 2002(10): 1613-1616
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

Joji Nishikido*a, Masayuki Nanboa, Akihiro Yoshidaa, Hitoshi Nakajimaa, Yousuke Matsumotob, Koichi Mikami*b
The Noguchi Institute, Tokyo 173-0003, Japan
Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo 152-8552
Fax: +81(3)57342776; e-Mail: kmikami@o.cc.titech.ac.jp;
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Publikationsverlauf

Received 1 July 2002
Publikationsdatum:
23. September 2002 (online)

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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

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16

Comm. available from Aldrich Chemical Company, Inc.: Cat. No. 33, 256-9.

18

The 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%.