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A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under “On‐Water” Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds
Author(s) -
De Rosa Margherita,
La Manna Pellegrino,
Soriente Annunziata,
Gaeta Carmine,
Talotta Carmen,
Hickey Neal,
Geremia Silvano,
Neri Placido
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701247
Subject(s) - furan , chemistry , catalysis , aldol reaction , hydrogen bond , stereoselectivity , combinatorial chemistry , computational chemistry , organic chemistry , molecule
The simple tetraminocalix[4]arene 1 , which contains weak H‐bond‐donor NH 2 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.