Lithiation and stereoselective transformations of 3-aroyl-2,2,4,4tetramethyloxazolidines (TMO amides), a new class of acid-labile atropisomeric amides

Mark Anstiss, Jonathan Clayden*, Alexander Grube, Latifa H. Youssef

*Corresponding author for this work

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

11 Citations (Scopus)

Abstract

Aromatic amides 4 (3-aroyl-2,2,4,4-tetramethyloxazolidines or TMO amides) derived by acylation of 2,2,4,4-tetramethyloxazolidine 6 undergo ortho- and lateral lithiation reactions. Given sufficient steric hindrance to bond rotation, they exhibit atropisomerism about the Ar-CO bond and the Ar-CO axis is able to control the atroposelective formation of new stereogenic centres. Unlike amides derived from hindered secondary amines such as diisopropylamine, the 3-aroyl-2,2,4,4-tetramethyloxazolidines are acid-sensitive, and treatment with methanesulfonic acid gives lactones or lactams by cyclisation onto the amide group.

Original languageEnglish
Pages (from-to)290-294
Number of pages5
JournalSYNLETT
Issue number2
DOIs
Publication statusPublished - Feb 2002

Keywords

  • Amides
  • Atropisomerism
  • Lactones
  • Lithiation
  • Stereoselectivity

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