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Sensing Remote Chirality: Stereochemical Determination of β‐, γ‐, and δ‐Chiral Carboxylic Acids
Author(s) -
Tanasova Marina,
Anyika Mercy,
Borhan Babak
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201410371
Subject(s) - stereocenter , porphyrin , chirality (physics) , chemistry , carboxylic acid , substrate (aquarium) , cotton effect , helicity , absolute configuration , stereochemistry , molecule , sign (mathematics) , enantioselective synthesis , chiral symmetry , circular dichroism , photochemistry , organic chemistry , physics , catalysis , mathematics , mathematical analysis , oceanography , particle physics , quantum mechanics , quark , geology , nambu–jona lasinio model
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.