Synthesis of (-)-(S, S)-clemastine by invertive N → C aryl migration in a lithiated carbamate

Anne M. Fournier, Robert A. Brown, William Farnaby, Hideki Miyatake-Ondozabal, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

44 Citations (Scopus)

Abstract

The first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer, has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of α-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement.

Original languageEnglish
Pages (from-to)2222-2225
Number of pages4
JournalOrganic Letters
Volume12
Issue number10
Early online date20 Apr 2010
DOIs
Publication statusPublished - 21 May 2010

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