330798-45-3Relevant articles and documents
Synthesis of Enantiopure Homoallylic Ethers by Reagent Controlled Facial Selective Allylation of Chiral Ketones
Tietze, Lutz F.,Weigand, Berthold,Voelkel, Ludwig,Wulff, Christian,Bittner, Christian
, p. 161 - 168 (2001)
The stereoselective allylation of chiral methyl ketones to give tertiary homoallylic ethers, which can easily be transformed into homoallylic alcohols, is described. Reaction of the enantiopure ketones 8a-d and the racemic ketones 26a-d with the norpseudoephedrine derivative 2 or ent-2 and allylsilane in the presence of a catalytic amount of trifluoromethanesulfonic acid, led to a series of homoallylic ethers with good to excellent diastereoselectivity (85:15 to > 97:3). The allylation is reagent controlled and nearly independent from the stereogenic centers in the substrates. A partial kinetic resolution was observed using the racemic ketones 26a-d. In the reaction of the chiral ketones 8a-d with the achiral reagents ethoxytrimethylsilane and allylsilane only a low diastereoselectivity was observed.