790291-07-5Relevant academic research and scientific papers
Facial-selective allylation of methyl ketones for the asymmetric synthesis of tertiary homoallylic ethers
Tietze, Lutz F.,Hoelsken, Soeren,Adrio, Jens,Kinzel, Tom,Wegner, Christoph
, p. 2236 - 2239 (2004)
The stereoselective allylation of methyl ketones is described to give tertiary homoallylic ethers, which can easily be transformed into homoallylic alcohols by a Birch reduction. Reaction of methyl ketones 4 with allylsilane 5 in the presence of the chiral TMS ether 3a and a catalytic amount of trifluoromethanesulfonic acid led to homoallylic ethers 6 in high yield with a selectivity of 9:1 to >20:1. The TMS ether 3a was prepared from inexpensive mandelic acid, which is commercially available in both enantiomeric forms, in four steps.
