Recognition and Organocatalysis with a Synthetic Cavitand Receptor

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2009 May 28

PMID 19469579

Citations 14

Authors

Fernando R Pinacho Crisostomo

Agusti Lledo

Siddhartha R Shenoy

Tetsuo Iwasawa

Julius Rebek Jr

Affiliations

Soon will be listed here.

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.

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