60623-95-2Relevant academic research and scientific papers
One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents
Downey, C. Wade,Dixon, Grant J.,Ingersoll, Jared A.,Fuller, Claire N.,MacCormac, Kenneth W.,Takashima, Anna,Sediqui, Rohina
supporting information, (2019/10/14)
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.
Convenient and direct azidation of sec -benzyl alcohols by trimethylsilyl azide with bismuth(III) triflate catalyst
Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Thongaram, Phanida,Kaewmee, Benyapa
, (2015/01/30)
Sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.
Convenient and direct azidation of sec -benzyl alcohols by trimethylsilyl azide with bismuth(III) triflate catalyst
Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Thongaram, Phanida,Kaewmee, Benyapa
, p. 323 - 329 (2015/02/19)
Sec-Benzyl azides were efficiently prepared by bismuth(III)-catalyzed direct azidation of sec-benzyl alcohols. The reaction was applied to a variety of substrates to provide the desired products in up to 99% yield within a short reaction time.
Mesoporous aluminosilicate-catalyzed Mukaiyama aldol reaction of aldehydes and acetals
Ito, Suguru,Tanuma, Kenji,Matsuda, Kohei,Hayashi, Akira,Komai, Hirotomo,Kubota, Yoshihiro,Asami, Masatoshi
, p. 8498 - 8504 (2014/12/11)
A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both aldehydes and acetals with silyl enol ethers or ketene silyl acetals to give the corresponding aldol adducts in moderate to high yields. The remarkable high catalytic activity of Al-MCM-41 over amorphous silica-alumina and aluminum-free mesoporous silicate was observed in the reaction. The solid acid catalyst could be recovered easily by filtration and the recovered catalyst was reusable in the same reactions without a significant loss of catalytic activity.
InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates
Onishi, Yoshiharu,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
, p. 2762 - 2765 (2011/08/02)
A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.
The Mukaiyama aldol and Mukaiyama-Michael reactions promoted by commercially available molecular sieves
Anada, Masahiro,Washio, Takuya,Watanabe, Yudai,Hashimoto, Shunichi
experimental part, p. 1489 - 1503 (2010/10/20)
The Mukaiyama aldol reaction of silyl ketene acetals with aldehydes has been effected by using commercially available 4 molecular sieves (4 MS) as a promoter. Various silyl ketene acetals and silyl enol ethers have been shown to be effective nucleophiles
Reactivity of silylated compounds with active methylene under microwave irradiation in heterogeneous dry media; application to the alkali metal fluoride-mediated silyl-Reformatsky reaction
Latouche, R.,Texier-Boullet, F.,Hamelin, J.
, p. 535 - 546 (2007/10/02)
The condensation of trimethylsilylacetic compounds 2a, 2b, (nitrile, ester) and trimethylsilylmethylphosphonic esters 2c with aromatic aldehydes 1, in the presence of alkali metal fluorides (potassium, cesium) unsupported or supported on alumina, magnesium oxide or clay (montmorillonite K10), is achieved by solvent-free techniques in a domestic microwave oven.The factors governing the reaction selectivity are studied.The silyl-Reformatsky reaction takes place in the presence of dried fluoride and leads to the silylated compound 3, which can be subsequently hydrolyzed to 4.The latter can be dehydrated to give the alkene 5.Keywords - alkali metal fluoride / silyl-Reformatsky reaction / nucleophilic activation / inorganic solid supports / trimethylsilyl-acetic compounds / microwave irradiation
ALKALI METAL FLUORIDE MEDIATED SILYL-REFORMATSKY REACTION IN SOLID-LIQUID MEDIA; ACTIVATION BY MICROWAVES.
Latouche, Regine,Texier-Boullet, Francoise,Hamelin, Jack
, p. 1179 - 1182 (2007/10/02)
Condensation of trimethylsilylacetonitrile or ethyltrimethylsilylacetate with benzaldehyde, in the presence of dried alkali metal fluorides in heterogeneous media under microwaves leads readily to β-trimethylsilyloxynitrile or ester according to a Reformatsky type reaction.The later products could be hydrolyzed and dehydrated on the wet inorganic salt to give the corresponding alkenes.
