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Host–Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry
Author(s) -
Gholami Hadi,
Anyika Mercy,
Zhang Jun,
Vasileiou Chrysoula,
Borhan Babak
Publication year - 2016
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.201601064
Subject(s) - cyanohydrin , chemistry , absolute configuration , circular dichroism , porphyrin , stereochemistry , photochemistry , organic chemistry , catalysis
The absolute stereochemistry of cyanohydrins, derived from ketones and aldehydes, is obtained routinely, in a microscale and derivatization‐free manner, upon their complexation with Zn‐MAPOL, a zincated porphyrin host with a binding pocket comprised of a biphenol core. The host–guest complex leads to observable exciton‐coupled circular dichroism (ECCD), the sign of which is easily correlated to the absolute stereochemistry of the bound cyanohydrin. A working model, based on the ECCD signal of cyanohydrins with known configuration, is proposed.