Synthesis of a New Chiral Sulfonic Acid

Abstract

A convenient route to an original chiral sulfonic acid is disclosed. The synthesis is based on an optimized and regioselective direct bis-orthoarylation of a commercially available phenol, followed by a Newman–Kwart rearrangement. Resolution by preparative chiral HPLC and oxidative cleavage give the targeted Brønsted acid in >99% ee.

Key words

Brønsted acid - sulfonic acid - Pinhey–Barton reaction - Newman–Kwart rearrangement - synthesis

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