Enantioselective Intramolecular α-Arylation of Benzylamine Derivatives: Synthesis of a Precursor to Levocetirizine
Abstract
A practical, transition metal-free method allows the enantioselective synthesis of α,α-diarylmethylamines by asymmetric α-arylation of benzylamines. Enantioselective lithiation of N'-aryl-N-benzyl-N-isopropyl ureas using a chiral lithium amide base generates a benzyllithium that undergoes an unactivated stereospecific intramolecular nucleophilic aromatic substitution to generate an α,α-diarylmethylamine in the form of its urea derivative, in up to >99% ee. Treatment with acid induces an 'azatropic shift' with retention of configuration, the product of which may be hydrolysed to the target amine.
Read the paper
Related studies
- Artificial Intelligence in Medicine: Cross-Sectional Study Among Medical Students on Application, Education, and Ethical Aspects
- Information quality of videos related to esophageal cancer on tiktok, kwai, and bilibili: a cross-sectional study
- The quality and reliability of short videos about hypertension on TikTok: a cross-sectional study
- Quality and reliability evaluation of pancreatic cancer-related video content on social short video platforms: a cross-sectional study
- Quality and reliability of pediatric pneumonia related short videos on mainstream platforms: cross-sectional study
- Association between metabolic score for insulin resistance (METS-IR) and hypertension: a cross-sectional study based on NHANES 2007–2018
Go deeper in Evidence Hub
Evidence Hub adds a study data sheet (design, sample size, evidence level, key numbers), an AI summary and a chat grounded in the paper's text.