Stereospecific formation of tetrasubstituted centres from trisubstituted centres during dearomatising anionic cyclisations

Ryan A. Bragg, Jonathan Clayden*

*Corresponding author for this work

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

34 Citations (Scopus)

Abstract

Dearomatising anionic cyclisation of tertiary naphthamides bearing chiral N-substituents (such as α-methylbenzyl) proceeds with overall retention of configuration at the newly formed tetrasubstituted chiral centre. The cyclisation is stereospecific overall, with the configuration of the starting trisubstituted stereogenic centre controlling the stereochemistry of the product. Highly substituted pyrrolidinone rings may be formed as single enantiomers from enantiomerically pure starting materials.

Original languageEnglish
Pages (from-to)8323-8326
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number48
DOIs
Publication statusPublished - 26 Nov 1999

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