A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under 'On-Water' Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds.

The simple tetraminocalix[4]arene 1, which contains weak H-bond-donor NH₂ groups, is reported to be a highly efficient organocatalyst for the Vinylogous Mukaiyama Aldol Reaction (VMAR) of 2-(trimethylsilyloxy)furan 5 with α-ketoesters 6 a- l under 'on-water' conditions owing to the hydrophobic amplification of weak H-bond interactions. The catalytic efficiency of calixarene catalyst 1 was shown to be closely related to its recognition abilities towards the reactants 5 and 6 through a multipoint recognition model. The proposed model provided good explanations for the differences on the reaction rate acceleration and on the stereoselectivity observed with different substrates. [ABSTRACT FROM AUTHOR]