T. Mukaiyama, S. Kobayashi
Feb 6, 1990
Citations
0
Influential Citations
26
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Three new carbon-carbon bond forming reactions by the use of new catalyst systems involving tin(II) compounds are described in this article. The aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones are catalyzed by the combination of a neutral molecule, trityl chloride, and a weak Lewis acid, tin(II) chloride, under extremely mild conditions. Similarly, an active species is generated by the combination of a Lewis acid and a tin(II) compound, for example, α,β-unsaturated thioesters smoothly react with silyl enol ethers to afford the corresponding Michael adducts stereoselectively in high yields by combined use of antimony(V) chloride and tin(II) triflate. Thirdly, a new chiral promoter has developed based on this concept of combination. Highly enantioselective aldol reaction between both achiral silyl enol ethers of thioesters and aldehydes is performed by combined use of chiral diamine coordinated tin(II) triflate and tributyltin fluoride.