Sensing remote chirality: Stereochemical determination of β‐, γ‐, and δ‐chiral carboxylic acids
Document Type
Article
Publication Date
2-12-2015
Department
Department of Chemistry
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.
Publication Title
Angewedte Chemie International Edition
Recommended Citation
Tanasova, M.,
Anyika, M.,
&
Borhan, B.
(2015).
Sensing remote chirality: Stereochemical determination of β‐, γ‐, and δ‐chiral carboxylic acids.
Angewedte Chemie International Edition,
54(14), 4274-4278.
http://doi.org/10.1002/anie.201410371
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/1305
