17875-59-1

Upstream product

• 100-52-7 benzaldehyde 
• 31469-16-6 1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene 

Downstream Products

• 52178-65-1 (R)-ethyl 2,2-dimethyl-3-hydroxy-3-phenylpropanoate 
• 133270-73-2 (S)-ethyl 2,2-dimethyl-3-hydroxy-3-phenylpropanoate 
• 52178-65-1 ethyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate 

Relevant academic research and scientific papers

Chemoselective aldol condensation in 5 mol dm 3 lithium perchlorate-nitromethane. A comparison with lithium perchloratediethyl ether medium

Aldol reactions of silyl enol ethers with aldehydes proceed in 5 mol dm 3 lithium perchlorate-nitromethane medium at ambient temperature. The reaction is highly chemoselective such that only aldehydes and cyclic ketones reacted while acyclic and aromatic ketones failed to react. The same reaction is not promoted in 5 mol dm"3 lithium perchlorate-diethyl ether medium. The difference between these two media is explained by the increased Lewis acidity of the lithium ion in nitromethane compared to that in ether.

Mukaiyama Aldol Reactions Catalyzed by Zirconocene Bis(triflate) Complexes: Stereochemistry and Mechanisms for C-C Bond Formation

The aldol condensations of α- and β-(benzyloxy) aldehydes with enol silanes, catalyzed by Cp2Zr(OTf)2THF or Cp2Zr(OTf)2, in a variety of solvents were studied. The simple diastereoselectivity of these reactions is modest and comparable to that observed using simple aldehydes of similar steric requirements. Studies have revealed that TMSOTf is directly produced on reaction with the zirconocene catalyst with the enol silane in nitroalkane solvent or is formed during catalysis in dichloromethane solution. Although TMSOTf is known to catalyze cross-aldol reactions under these conditions, the rate of this process is not always competitive with that observed using the zirconocene catalysts. In particular, sterically unhindered or aromatic aldehydes react via a mechanism that appears to be mainly Zr-catalyzed, based on both the difference in rate between Zr- and Si-mediated reactions as well as differences in enol silane/silyl triflate reactivity in crossover-type experiments. With sterically hindered aldehydes in dichloromethane or nitromethane, catalysis is mediated by Si. The Zr-catalyzed process occurs via formation of a Zr-aldolate complex from aldehyde and enol silane, with liberation of TMSOTf, followed by rate-limiting O-silylation of the metal aldolate by TMSOTf, as revealed by both model studies and in situ monitoring during catalysis.

Iron complexes as catalysts in aldol additions

(Dicarbonyl)(η5-cyclopentadienyl) iron halides function as catalysts for the aldol addition of enosilanes to aldehydes.

ALDOL REACTIONS, CONJUGATE ADDITIONS, AND ALKYLATION REACTIONS OF O-SILYLATED KETENE ACETALS UNDER NEUTRAL CONDITIONS

Aldol reactions, conjugate additions, and alkylation reactions of O-silylated ketene acetals take place under neutral conditions by using a high pressure technique.