Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

Jonathan Clayden*, Megan Darbyshire, Jennifer H. Pink, Neil Westlund, Francis X. Wilson

*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.

Original languageEnglish
Pages (from-to)8587-8590
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number49
DOIs
Publication statusPublished - 8 Dec 1997

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