Recognition and organocatalysis with a synthetic cavitand receptor.
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.
Pinacho Crisóstomo
Fernando R
FR
The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Lledó
Agustí
A
Shenoy
Siddhartha R
SR
Iwasawa
Tetsuo
T
Rebek
Julius
J
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds; D004988:Ethers, Cyclic / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D012118:Resorcinols / Q000737:chemistry*
D000438:Alcohols; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D012118:Resorcinols; C442939:cavitand