Diastereoisomeric atropisomers of peri-substituted naphthamides: Synthesis, stereoselectivity and stability

Jonathan Clayden*, Neil Westlund, Francis X. Wilson

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

13 Citations (Scopus)

Abstract

8-Formyl-1-naphthamides can be made by perilithiation of 1-(dimethylaminomethyl)-naphthalene, quenching the organolithium with a carbamoyl chloride and subjecting the product amine to a Polonovski reaction. The naphthamides react stereoselectively with nucleophiles to give predominantly the syn atropisomers of the product alcohols. Oxidation gives ketones which also give mainly the syn atropisomer on reduction. The rate of thermal epimerisation of the products is high relative to 2-substituted 1-naphthamides: the barrier to Ar-CO rotation is ca. 90 kJ mol-1.

Original languageEnglish
Pages (from-to)7883-7887
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number45
DOIs
Publication statusPublished - 5 Nov 1999

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