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Inherently Chiral Resorcin[4]arenes with Urea and Amide Side Arms: Synthesis, Structure and Chiral Recognition
Author(s) -
Wiegmann Sebastian,
Fukuhara Gaku,
Neumann Beate,
Stammler HansGeorg,
Inoue Yoshihisa,
Mattay Jochen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201272
Subject(s) - chemistry , diastereomer , amide , circular dichroism , urea , titration , mandelic acid , molecular recognition , stereochemistry , combinatorial chemistry , organic chemistry , molecule
Starting from an inherently chiral aminomethyl‐substituted resorcin[4]arene, a series of urea and amide derivatives were synthesized; these new functionalities extend the macrocycle cavity and introduce new opportunities for chiral recognition. A pair of diastereomeric macrocycles was obtained by introducing ( S )‐(–)‐1‐phenylethyl‐urea functionalities. Chiral recognition capabilities of the diastereomeric hosts were investigated by circular dichroism spectral titration to reveal modest R / S selectivities of up to 1.4 for mandelic acid and other related carboxylic guests.