Recognition and organocatalysis with a synthetic cavitand receptor.

Recognition and organocatalysis with a synthetic cavitand receptor.
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DOI:
10.1021/ja900766b
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发表时间:
2009-06-03
影响因子:
15
通讯作者:
Rebek J Jr
Rebek J Jr
中科院分区:
化学1区
文献类型:
--
作者:
Pinacho Crisóstomo FR;Lledó A;Shenoy SR;Iwasawa T;Rebek J Jr

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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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