On the Stereoselective Opening of Chiral Dioxane Acetals. Nucleophile Dependence

Scott E. Denmark, Neil G. Almstead

Research output: Contribution to journalArticle

Abstract

The stereoselective allylation of chiral dioxane acetals 1 was found to be highly dependent on the nature of allylmetal reagent in the following order: Ph3Si (19/1) < Me3Si (58/1) < Ph3Sn (90/1) < Me3Ge (100/1) < n-Bu3Sn (>300/1). The allylation with allyltributylstannane was significantly more selective than allyltrimethylsilane for a number of chiral dioxane acetals examined.

Original languageEnglish (US)
Pages (from-to)6485-6487
Number of pages3
JournalJournal of Organic Chemistry
Volume56
Issue number23
DOIs
StatePublished - Nov 1 1991

ASJC Scopus subject areas

  • Organic Chemistry

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