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DOI: 10.1055/s-2008-1077818
Organocatalytic Ring-Opening Reactions in a Molecular Vessel
S. R. Shenoy, F. R. Pinacho Crisóstomo, T. Iwasawa, Jr. J. Rebek, *
The Scripps Research Institute, La Jolla, USA
Publication History
Publication Date:
20 June 2008 (online)

Significance
The highly regioselective ring opening of epoxides, like 1, yielding exo product 2a, assisted by the vase-like resorcinarene scaffold receptor 3 is reported. Species 3 contains a catalytically active carboxylic acid functionality on its concave inner surface. Complementary, the reaction was conducted in the presence of non-cavitative model acid catalyst 4. The significantly faster reaction using 3, shows that its sophisticated architecture, with hydrogen-bonding and π-stacking domains in the scaffold is beneficial for the regioselective transformation of host substrate 1. These diverse interaction modes were also interpreted to be responsible for the comparatively higher product selectivity, in favor of 5-exo product 2a.