Sensing Remote Chirality: Stereochemical Determination of β‐, γ‐, and δ‐Chiral Carboxylic Acids |
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Authors: | Prof. Dr. Marina Tanasova Dr. Mercy Anyika Prof. Dr. Babak Borhan |
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Affiliation: | 1. Department of Chemistry, Michigan Technological University, 1400 Townsend Dr, Houghton, MI 49931 (USA);2. Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall drive, Lawrence, KS 66045 (USA);3. Department of Chemistry, Michigan State University, East‐Lansing, MI 48824 (USA) |
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Abstract: | Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β‐, γ‐, or δ‐chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner. |
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Keywords: | chirality circular dichroism host– guest systems stereochemistry zinc |
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