Host-Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry.
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.
Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Hadi
H
Gholami
Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Mercy
M
Anyika
Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Jun
J
Zhang
Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Chrysoula
C
Vasileiou
Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA. babak@chemistry.msu.edu.
Babak
http://orcid.org/0000-0002-3193-0732
B
Borhan
ECCD; MAPOL; circular dichroism; cyanohydrin; stereochemistry