73739-29-4Relevant academic research and scientific papers
Highly diastereoselective reformatsky-type reaction promoted by tin iodide Ate complex
Shibata, Ikuya,Suwa, Toshihiro,Sakakibara, Hideaki,Baba, Akio
, p. 301 - 303 (2002)
Chemical equation presented An ate type of tin complex, Li+[n-Bu2Snl3]-/HMPA, works as a novel type of reagent to accomplish the highly diastereoselective Reformatsky-type reaction by the halogen-metal exchange method.
Method for Performing Aldol Reaction in Water
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Page/Page column 4, (2008/06/13)
An aldol reaction in an aqueous solution between an aldehyde represented by the following formula (I): [in-line-formulae]R—CHO??(I) [/in-line-formulae] (wherein R is a hydrocarbon group which may have an substituent), and a silicon enolate represented by
Ammonium phenoxides-catalyzed syn-selective aldol reaction between an aldehyde and an trimethylsilyl enolate
Fujisawa, Hidehiko,Nagata, Yuzo,Sato, Yoshinori,Mukaiyama, Teruaki
, p. 842 - 843 (2007/10/03)
Aldol reactions between aldehydes and trimethylsilyl enolates generated from ketones or thioesters proceeded smoothly in the presence of a Lewis base catalyst such as tetrabutylammonium phenoxide or p-methoxyphenoxide in THF to afford the corresponding al
Stereoselective crossed aldol reaction via boron enolates generated from α-iodo ketones and 9-borabicyclo[3.3.1]nonane
Mukaiyama, Teruaki,Takuwa, Tomofumi,Yamane, Keiko,Imachi, Shouhei
, p. 813 - 823 (2007/10/03)
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.
Lewis base-promoted aldol reaction of dimethylsilyl enolates in aqueous dimethylformamide: Use of calcium chloride as a Lewis base catalyst
Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
, p. 536 - 537 (2007/10/03)
In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin. Copyright
Stereoselective crossed aldol reaction via boron enolate generated from α-iodoketones and 9-BBN-H
Mukaiyama, Teruaki,Imachi, Shouhei,Yamane, Keiko,Mizuta, Masahiro
, p. 698 - 699 (2007/10/03)
Boron enolates were in situ generated smoothly by treating α-iodo ketones with 9-BBN-H, and aldols were produced in highly diastereoselective manner by successive reaction with various aldehydes at low temperature.
Catalytic use of a boron source for boron enolate mediated stereoselective aldol reactions in water
Mori, Yuichiro,Manabe, Kei,Kobayashi
, p. 2816 - 2818 (2007/10/03)
Use of boron enolates in water! Boron enolates can be generated and used for aldol reactions in water by using a catalytic amount of Ph2BOH (see scheme). This is the first example of a catalytic use of a boron enolates. The mechanism of the rea
Diastereoselective aldol reaction of α-bromo ketones with aliphatic aldehydes by using titanium(II) chloride and copper
Mukaiyama, Teruaki,Kagayama, Akifumi,Igarashi, Koji,Shiina, Isamu
, p. 1157 - 1158 (2007/10/03)
Highly diastereoselective aldol reaction of α-bromo ketones with aliphatic aldehydes was successfully carried out by using titanium(II) chloride and copper in dichloromethane at low temperature. Similarly, Reformatsky-type reaction of α-bromo thioester with aliphatic aldehydes was promoted under mild conditions to afford β-hydroxy thioesters in good to moderate yields.
Scandium trisdodecylsulfate (STDS). A new type of Lewis acid that forms stable dispersion systems with organic substrates in water and accelerates aldol reactions much faster in water than in organic solvents
Kobayashi, Shu,Wakabayashi, Takeshi
, p. 5389 - 5392 (2007/10/03)
A new type of Lewis acid, scandium trisdodecylsulfate (STDS), was prepared. In the presence of a catalytic amount of STDS, aldol reactions of silyl enol ethers with aldehydes proceeded smoothly in water without using any organic solvents. It was proven th
Uncatalyzed aldol reaction using a dimethylsilyl enolate and α- dimethylsilyl ester in N,N-dimethylformamide
Miura, Katsukiyo,Sato, Hiroshi,Tamaki, Kentaro,Ito, Hajime,Hosomi, Akira
, p. 2585 - 2588 (2007/10/03)
Dimethylsilyl enolates and α-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction.
