Allylindation of cyclopropenes in organic and aqueous media: switching theregio- and stereoselectivity based on the chelation with a hydroxyl group and the crystal structure of the cyclopropylindium product

Citation
S. Araki et al., Allylindation of cyclopropenes in organic and aqueous media: switching theregio- and stereoselectivity based on the chelation with a hydroxyl group and the crystal structure of the cyclopropylindium product, CHEM-EUR J, 7(13), 2001, pp. 2784-2790
Citations number
43
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
0947-6539 → ACNP
Volume
7
Issue
13
Year of publication
2001
Pages
2784 - 2790
Database
ISI
SICI code
0947-6539(20010702)7:13<2784:AOCIOA>2.0.ZU;2-6
Abstract
Hydroxy-bearing cyclopropenes react with allylindium reagents to undergo cl ean allylindation both in organic and aqueous media, in which the chelation of the hydroxyl group to indium plays the central role. The regio-and ster eoselectivity have been regulated both by the location of the hydroxyl grou p in the molecules and the reaction solvents. In particular, the allylindat ion in water shows marked differences from that in organic solvents; the re gio- and stereoselectivity have totally been reversed compared with those i n organic solvents. Unusually stable cyclopropylindium compounds have been isolated from the reaction of 1-(omega -hydroxyalkyl)-cyclopropenes and the structure has fully been established by X-ray crystallography.