An unusual intramolecular acetal alkylation

Xiuchun Gao, Punit P. Seth, John K. Bitok, Nancy I. Totah

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

Upon treatment with Grignard reagents, suitably functionalized cis-fused bicyclic ketone acetals undergo intramolecular acetal alkylation to provide oxabicyclo[3.3.1]nonane derivatives. This transformation results in the formation of up to three stereogenic centers with high levels of stereoselectivity. Product distribution and stereochemistry vary with substrate substitution and the Grignard reagent utilized.

Original languageEnglish (US)
Pages (from-to)819-823
Number of pages5
JournalSynlett
Issue number5
DOIs
StatePublished - Mar 21 2005

Keywords

  • Acetals
  • Alkylation
  • Annulation
  • Grignard reagents
  • Stereoselectivity

ASJC Scopus subject areas

  • Organic Chemistry

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