Enantioselective Intramolecular α‐Arylation of Benzylamine Derivatives: Synthesis of a Precursor to Levocetirizine

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Enantioselective Intramolecular α‐Arylation of Benzylamine Derivatives: Synthesis of a Precursor to Levocetirizine ; day:23 ; month:02 ; year:2023 ; extent:7
Angewandte Chemie ; (23.02.2023) (gesamt 7)

Creator: Saunthwal, Rakesh K.
Schwarz, Maria
Mallick, Rajendra K.
Terry‐Wright, William
Clayden, Jonathan

DOI: 10.1002/ange.202216758

URN: urn:nbn:de:101:1-2023022314163064408417

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:58 AM CEST

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Associated

Saunthwal, Rakesh K.
Schwarz, Maria
Mallick, Rajendra K.
Terry‐Wright, William
Clayden, Jonathan

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