title: Sensing remote chirality: stereochemical determination of β-, γ-, and δ-chiral carboxylic acids.
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.
authors: Department of Chemistry, Michigan Technological University, 1400 Townsend Dr, Houghton, MI 49931 (USA).
authors: Marina
authors: M
authors: Tanasova
authors: Mercy
authors: M
authors: Anyika
authors: Babak
authors: B
authors: Borhan
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids
keywords: chirality; circular dichroism; host-guest systems; stereochemistry; zinc