Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

Jonathan Clayden*, Neil Westlund, Christopher S. Frampton

*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

Restricted rotation about the Ar-CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-l-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisatiori, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.

Original languageEnglish
Pages (from-to)1379-1385
Number of pages7
JournalPerkin 1
Issue number9
DOIs
Publication statusPublished - 18 Apr 2000

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