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
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
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.