13161-18-7Relevant academic research and scientific papers
Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
Bahmanyar,Houk,Martin, Harry J.,List, Benjamin
, p. 2475 - 2479 (2003)
Quantum mechanical calculations were employed to predict the ratio of four stereoisomeric products expected from two complex reactions involving the aldol reactions of cyclohexanone with benzaldehyde or with isobutyraldehyde catalyzed by (S)-proline. Expe
Indium trichloride catalysed Mukaiyama aldol reaction in water
Loh, Teck-Peng,Pei, Jian,Cao, Guo-Qiang
, p. 1819 - 1820 (1996)
In the presence of a catalytic amount of indium(III) chloride (InCl3) (20 mol%), aldehydes react smoothly with ketone trimethylsilyl enol ethers in water to afford the corresponding aldol adducts in good yields.
Solvent-effects tuning the catalytic reactivity of prolinamides in asymmetric aldol reactions
Huang, Xiang-Rong,Liu, Qi,Wang, Jing,Xiao, Jun-An,Yang, Hua
, p. 1590 - 1598 (2014)
Novel prolinamides were prepared and applied as organocatalysts in the asymmetric aldol reaction. Stable imidazolidinones were formed between prolinamides and aromatic aldehydes in organic solvents. It was found that aqueous conditions can significantly suppress the formation of the unwanted imidazolidinone intermediate and improve the catalytic activity of the prolinamides. As a consequence, high chemical yields (up to 99%) and good diastereoselectivity (up to >20:1 dr) and enantioselectivity (up to 95% ee) were achieved in 2-Me-THF or brine. This strategy could serve as a general solution to enhance the performance of prolinamides as organocatalysts.
Indium-trichloride catalyzed Mukaiyama-aldol reaction in water: Solubility, aggregation and internal pressure effect
Loh, Teck-Peng,Pei, Jian,Koh, Kevin Siong-Ve,Cao, Guo-Qiang,Li, Xu-Ran
, p. 3465 - 3468 (1997)
Studies on the effects of water and the binding characteristic of InCl3, in the Mukaiyama-aldol reaction with an in depth mechanistic probe on the probable internal pressure and aggregation effects exerted in this media.
Diastereoselective sulfur ylide promoted aldol/epoxidation
Hansen, Jeffrey A.,Smith, Colin R.,Linder, Ryan J.,Huffman, John C.
, p. 7209 - 7212 (2006)
A mixture of cyclohexanone or 4-methylcyclohexanone and an aromatic aldehyde is treated with dimethylsulfoxonium methylide to effect a tandem aldol/epoxidation reaction. The resulting product contains three or four new stereocenters but only one of the po
Preparation of Enolates from α-Haloketones with n-BuLi, PhMgBr, or Et2Zn via Halogen-Metal Exchange Reaction
Aoki, Yoshitaka,Oshima, Koichiro,Utimoto, Kiitiro
, p. 463 - 464 (1995)
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.
ERYTHRO SELECTIVE ALDOL REACTION OF α-TRICHLOROSTANNYL KETONES
Nakamura, Eiichi,Kuwajima, Isao
, p. 3347 - 3350 (1983)
The aldol reaction of α-stannyl ketones with aromatic and aliphatic aldehydes is highly (up to 95percent) erythro selective.
New Crossed Aldol Reaction. Reaction of Enamines with Aldehydes Activated by Lewis Acids
Takazawa, Osamu,Kogami, Kunio,Hayashi, Kazuo
, p. 2427 - 2428 (1985)
Enamines react with aldehydes in the presence of Lewis acids such as BF3*OEt2 to give the corresponding crossed aldol products in good yields.Reaction of dienamines with aldehydes gives the corresponding β, γ-unsaturated α-(1-hydroxyalkyl) carbonyl compou
Stereochemistry of aldols: Configuration and conformation of aldols derived from cycloalkanones and aldehydes
Kitamura,Nakano,Miki,Okada,Noyori
, p. 8939 - 8950 (2001)
The structures of cycloalkanone-based threo and erythro aldols were investigated by systematic introduction of stereo-determining factors. The combination of single-crystal X-ray analysis and cryoscopic measurement and solution NMR and IR studies elucidat
Lewis acid promoted ene-like reactions of enol ethers with aldehydes
Shoda,Nakamura,Tanino,Kuwajima
, p. 6281 - 6284 (1993)
Use of organoaluminum reagents induces ene-like reactions of enol silyl ethers with aldehydes, and enols having bulky silyl groups selectively afforded syn adducts.
