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[2.2]Paracyclophane‐Derived Planar‐Chiral Hydrogen‐Bond Receptors
Author(s) -
Schneider Jakob F.,
Fröhlich Roland,
Paradies Jan
Publication year - 2012
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100082
Subject(s) - enantiopure drug , chemistry , thiourea , hydrogen bond , tetramethylammonium , combinatorial chemistry , catalysis , organic chemistry , enantioselective synthesis , molecule , ion
The development of planar‐chiral hydrogen‐bond donors based on the [2.2]paracyclophane scaffold is discussed. General strategies to access functionalized enantiopure [2.2]paracyclophane derivatives are briefly reviewed, with the focus on suitable precursors for the synthesis of planar‐chiral thiourea derivatives. The synthesis of fourteen hydrogen‐bond donors is described. The interaction of four thiourea derivatives with hydrogen‐bond acceptors (DMSO and tetramethylammonium chloride) was investigated by 1 H NMR spectroscopy and X‐ray crystallography. A selection of enantiomerically pure planar‐chiral derivatives was applied in asymmetric hydrogen‐bond catalysis.