Dynamically resolved peri-substituted 2-formyl naphthamides: A new class of atropisomeric chiral auxiliary

Jonathan Clayden*, Catherine McCarthy, John G. Cumming

*Corresponding author for this work

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

45 Citations (Scopus)

Abstract

2-Formyl-N,N-dialkylnaphthamides are chiral, atropisomeric compounds, provided they are substituted peri to the amide group. They may be obtained as single enantiomers by dynamic resolution on formation of diastereoisomeric aminal derivatives and used as chiral auxiliaries in a new addition/rearrangement strategy. Nucleophilic attack by vinyl anion equivalents in the presence of Lewis acids leads atroposelectively to single diastereoisomers of allylic alcohols, whose derivatives undergo stereospecific [3,3]-sigmatropic rearrangements. Reductive ozonolysis of the rearrangement product returns an enantiomerically pure functionalised alcohol and in principle allows recovery of the atropisomeric auxiliary. (C) 2000 Published by Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)3279-3283
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number18
DOIs
Publication statusPublished - 29 Apr 2000

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