75990-52-2

Upstream product

• 100-52-7 benzaldehyde 
• 611-70-1 phenyl isopropyl ketone 
• 39158-85-5 2-methyl-1-phenyl-1-trimethylsiloxy-1-propene 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 769-60-8 2-methyl-1-phenylprop-2-en-1-one 

Downstream Products

• 1337920-89-4 C₁₇H₁₈O₂ 
• 41169-42-0 2,2-dimethyl-1,3-diphenylpropane-1,3-dione 
• 41169-43-1 cis-3,3-dimethyl-1,2-diphenylcyclopropane-1,2-diol 

Relevant academic research and scientific papers

Lewis base-catalyzed conjugate reduction and reductive aldol reaction of α,β-unsaturated ketones using trichlorosilane

Lewis bases such as Ph3P=O and HMPA catalyze the 1,4-reduction of α,β-unsaturated ketones with trichlorosilane, and because the 1,2-reduction of aldehydes scarcely proceeded under the conditions, one-pot reductive aldol reactions with aldehydes were successfully achieved; preliminary studies using a chiral Lewis base revealed a high potential for enantioselective catalysis. The Royal Society of Chemistry.

Bismuth triflate catalyzed Mukaiyama aldol reaction in an ionic liquid

We have developed an efficient, bismuth triflate catalyzed Mukaiyama aldol reaction. The reaction proceeds rapidly and affords the corresponding β-hydroxy carbonyl compound in moderate to very good yields (up to 92%). Wiley-VCH Verlag GmbH & Co. KGaA, 200

Bismuth-mediated reductive dehalogenation of α-halocarbonyl compounds

Bismuth metal, activated by ammonium hydrogen fluoride, was found to reduce various α-halocarbonyl compounds efficiently and chemoselectively in aqueous media to give the dehalogenated reduction products in excellent yields.

Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane

Boron enolates were in situ-generated reductively by treating various α-iodo ketones such as 2-iodo-1-phenylpropan-1-one, 2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived from α-iodo ketones and pinacolatoborane were successfully isolated by distillation, though the yields were rather moderate.

Organometallic reactions in aqueous media - Bismuth-mediated crossed aldol type reactions

Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syndiastereoselective.

Preparation of Enolates from α-Haloketones with n-BuLi, PhMgBr, or Et2Zn via Halogen-Metal Exchange Reaction

Metal-halogen exchange of α-iodoketones was performed upon treatment with n-BuLi, PhMgBr, Et2Zn or Me3Al in ether at 0 deg C to give the corresponding metal enolates which reacted with aldehydes to provide the aldol type products in good yields.

Crossed Aldol Type Condensation Reactions in Aqueous Media

Directed crossed aldol type condensations can be carried out in aqueous media using α-halocarbonyl compounds, aldehydes, and metallic zinc or tin.

TRANSIENT TITANIUM ENOLATE ALDOL CONDENSATIONS

A convenient method is described for the generation and subsequent reaction of a proposed titanium enolate with aromatic aldehydes.