Axial chirality in xanthene-4,5-dicarboxamides: 1,9-stereocontrol mediated by remote interactions between conformationally constrained amide groups

Jonathan Clayden*, Martin N. Kenworthy, Latifa H. Youssef, Madeleine Helliwell

*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

Tertiary 9,9-dimethylxanthene-4,5-dicarboxamides have a C2-symmetric, axially chiral ground state due to remote interactions between the conformationally constrained tertiary amide substituents. Double ortholithiation-alkylation blocks amide rotation, and the 3,6-dialkylated products are chiral, existing as a pair of enantiomeric C2-symmetric atropisomers. Double lateral lithiation-electrophilic quench introduces a pair of 1,9-related stereogenic centres - each under the control of one of the conformationally constrained amides - with complete diastereoselectivity. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)5171-5175
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number27
DOIs
Publication statusPublished - 1 Jul 2000

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