Title

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

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