Atroposelectivity in the reactions of laterally lithiated tertiary amides

Jonathan Clayden*, Jennifer H. Pink

*Corresponding author for this work

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

43 Citations (Scopus)

Abstract

Lateral lithiation - electrophilic quench of 2-substituted N,N-dialkyl-1-naphthamides proceeds with high levels of diastereoselectivity in favour of one atropisomer of the product. Similar atroposelectivity may be observed in the reactions of 2-substituted benzamides, provided the products are trapped at low temperature by a subsequent in situ ortholithiation - alkylation reaction.

Original languageEnglish
Pages (from-to)2561-2564
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number14
DOIs
Publication statusPublished - 7 Apr 1997

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