Host–Guest Assembly of a Molecular Reporter with Chiral Cyanohydrins for Assignment of Absolute Stereochemistry |
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| Authors: | Hadi Gholami Dr Mercy Anyika Jun Zhang Dr Chrysoula Vasileiou Prof Dr Babak Borhan |
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| Affiliation: | Department of Chemistry, Michigan State University, E. Lansing, MI, USA |
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| Abstract: | 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. |
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| Keywords: | circular dichroism cyanohydrin ECCD MAPOL stereochemistry |
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