Allylation of methylenecyclopropanes with allylindium reagents

Methylenecyclopropanes carrying a hydroxymethyl group at the ring underwent stereoselective allylindation with allylindium sesquiiodide to afford the allylated products, in which the allyl group was delivered at the external sp 2 carbon via cyclopropylindium intermediates. The reaction of ethyl 2-cy...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 37; pp. 5411 - 5413
Main Authors Hirashita, Tsunehisa, Daikoku, Yusuke, Osaki, Hitoshi, Ogura, Mamiko, Araki, Shuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 08.09.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
INACTIVATION
ACYL-COA DEHYDROGENASE
STEREOSELECTIVE ALLYLINDATION
CARBOINDATION
ALKYLIDENECYCLOPROPANES
MECHANISM
(METHYLENECYCLOPROPYL)FORMYL-COA
CYCLOPROPENES
ALKYNOLS
CHELATION
Online AccessGet full text

Cover

More Information
Summary:Methylenecyclopropanes carrying a hydroxymethyl group at the ring underwent stereoselective allylindation with allylindium sesquiiodide to afford the allylated products, in which the allyl group was delivered at the external sp 2 carbon via cyclopropylindium intermediates. The reaction of ethyl 2-cyclopropylideneacetate and triallylindium afforded the 1,4-adduct along with dimeric products.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.07.009