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Recognition and organocatalysis with a synthetic cavitand receptor.

ABSTRACT: The cyclization reaction of an epoxyalcohol is catalyzed by a synthetic cavitand receptor with an inwardly directed carboxylic acid function. The receptor features a hydrophobic pocket in which the substrate is bound and positioned to react in a regioselective manner. The nature of this substrate-catalyst complex and its dynamic properties were investigated by NMR methods and with the aid of a model compound lacking the epoxide function. The kinetic parameters of the cyclization reaction were also studied. A catalytic cycle is proposed and diverse inhibition mechanisms are identified that parallel those encounterd in enzymology.

SUBMITTER: Pinacho Crisostomo FR

PROVIDER: S-EPMC2720318 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Recognition and organocatalysis with a synthetic cavitand receptor.

Pinacho Crisóstomo Fernando R FR Lledó Agustí A Shenoy Siddhartha R SR Iwasawa Tetsuo T Rebek Julius J

Journal of the American Chemical Society 20090601 21

The cyclization reaction of an epoxyalcohol is catalyzed by a synthetic cavitand receptor with an inwardly directed carboxylic acid function. The receptor features a hydrophobic pocket in which the substrate is bound and positioned to react in a regioselective manner. The nature of this substrate-catalyst complex and its dynamic properties were investigated by NMR methods and with the aid of a model compound lacking the epoxide function. The kinetic parameters of the cyclization reaction were al ...[more]

PMID: 19469579

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