Indium-mediated gamma-pentadienylation of aldehydes and ketones: Cross-conjugated trienes for diene-transmissive cycloadditions

Authors
Woo, S Squires, N Fallis, AG
Citation
S. Woo et al., Indium-mediated gamma-pentadienylation of aldehydes and ketones: Cross-conjugated trienes for diene-transmissive cycloadditions, ORG LETT, 1(4), 1999, pp. 573-575
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
4
Year of publication
1999
Pages
573 - 575
Database
ISI
SICI code
1523-7060(19990826)1:4<573:IGOAAK>2.0.ZU;2-4
Abstract
[GRAPHICS] Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of ca rbonyl compounds results in gamma-pentadienylation to generate the 1,4-dien e. Elimination of the resulting alcohol affords cross conjugated triene sys tems which rapidly react with appropriate dienophiles to give tandem interm olecular Diels-Alder adducts.