Mercury(II)-mediated routes to some side-chain functionalised 1,7-dioxaspiro[5.5]undecanes. Applications of Luche-Barbier chemoselective addition to ketoaldehydes

James J. De Voss*, Joanne F. Jamie, Joanne T. Blanchfield, Mary T. Fletcher, Michael G. O'Shea, William Kitching

*Corresponding author for this work

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The ketoaldehyde, 5-oxo-9-decenal (4) undergoes chemoselective addition to the aldehyde with either allyl or propargyl bromide under Luche-Barbier conditions. Oxymercuration-cyclisation of the resulting hydroxyketones, followed by reductive or oxidative demercuration, provides functionalised spiroacetals, some of which are of insect origin.

Original languageEnglish
Pages (from-to)1985-1996
Number of pages12
JournalTetrahedron
Volume47
Issue number10-11
DOIs
Publication statusPublished - 11 Mar 1991
Externally publishedYes

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