Diastereoisomeric atropisomers from the addition of lithiated N,N-dialkyl-l-naphthamides to aldehydes

Peter Bowles*, Jonathan Clayden, Matthew Tomkinson

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

44 Citations (Scopus)

Abstract

2-Substituted N,N-diethyl or N,N-diisopropyl 1-naphthamides exist as stable atropisomers. When the 2-substituent is a 1-hydroxyalkyl group, the atropisomers are separable diastereoisomers. Synthesis of these compounds by the addition of aldehydes to orholithiated N,N-dialkyl 1-naphthamides proceeds with moderate to good diastereoselectivity in favour of the aR*S* (syn) diastereoisomer.

Original languageEnglish
Pages (from-to)9219-9222
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number50
DOIs
Publication statusPublished - 11 Dec 1995

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