- FeCl3·6H2O-catalyzed mukaiyama-aldol type reactions of enolizable aldehydes and acetals
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Mukaiyama-aldol type reactions of acetals derived from enolizable aldehydes with FeCl3·6H2O, an eco-friendly, low-cost, and stable catalyst, lead to β-methoxycarbonyl compounds with nearly quantitative yields. The methodology is extended to the parent aldehydes as starting materials, leading to the corresponding aldols with lower yields, but efficiently. Different alkyl and aryl substituted acetals and aldehydes have been tested in the reaction with linear and cyclic silyl enol ethers. Reactions are carried out in an open air atmosphere, and additives are not required. Acetals can be considered activating groups of the carbonyl moiety rather than a protecting group in this type of FeCl3·6H2O-catalyzed condensation.
- Rodríguez-Gimeno, Alejandra,Cuenca, Ana B.,Gil-Tomás, Jesús,Medio-Simón, Mercedes,Olmos, Andrea,Asensio, Gregorio
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p. 8263 - 8270
(2015/03/18)
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- NOVEL BETA-HYDROXYKETONES AND BETA-ALKOXYKETONES WITH ESTROGENIC ACTIVITY
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This invention relates to β-hydroxyketones and β-alkoxyketones of formula (I), to their use as estrogen receptor modulators, and to methods for their preparation.
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Page/Page column 36
(2009/06/27)
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- Synthesis and evaluation of estrogen agonism of diaryl 4,5- dihydroisoxazoles, 3-hydroxyketones, 3-methoxyketones, and 1,3-diketones: A compound set forming a 4D molecular library
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In this paper, the preparation and systematic evaluation of estrogen receptor α (ERα) and estrogen receptor β (ERβ) activities of some diaryl-1,3-diones and their synthetic intermediates, diaryl-4,5-dihydroisoxazoles, diaryl-3-hydroxyketones, diaryl-3-met
- Pulkkinen, Juha T.,Honkakoski, Paavo,Per?kyl?, Mikael,Berczi, Istvan,Laatikainen, Reino
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supporting information; experimental part
p. 3562 - 3571
(2009/04/06)
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- L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones
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β-Alkoxy ketones were prepared by a one-pot three-component reaction of aliphatic aldehydes, ketones, and alcohols catalyzed by L-proline. Steric effects on the reaction were studied with substituted ketones, aldehydes, and alcohols, and the results indicate that reactions employing methyl ketones, α-unsubstituted aliphatic aldehydes and methanol produce the β-alkoxy ketones in the best yields when L-proline is used as the catalyst. The reaction mechanism is discussed. Georg Thieme Verlag Stuttgart.
- Dodda, Rajasekhar,Zhao, Cong-Gui
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p. 3238 - 3242
(2008/09/17)
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- Selective aldol reactions of acetals on mesoporous silica catalyst
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Mukaiyama-aldol reactions of carbonyl compounds with silyl enol ethers were well catalyzed on siliceous mesoporous materials (MCM-41). The reactivity of acetals was much higher than that of aldehyde. The reactions proceeded selectively at 273-298 K on the
- Ishitani, Haruro,Iwamoto, Masakazu
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p. 299 - 301
(2007/10/03)
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- Chemoselective aldol reaction of silyl enolates catalyzed by Mgl2 etherate
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(matrix presented) Mukaiyama-type aldol coupling of typical silyl enolates 2-4 with aryl or vinyl aldehydes and acetals was realized in the presence of 1-5 mol % of MgI2 etherate (1) in a mild, efficient, and highly chemoselective manner. Iodid
- Li, Wei-Dong Z.,Zhang, Xing-Xian
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p. 3485 - 3488
(2007/10/03)
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- Reversal Phenomena of the Preferential Activation of Aldehydes to the Corresponding Acetals under Non-Basic Conditions. The Chemoselective Aldol Reaction of Aldehydes with t-Butyldimethylsilyl Enol Ethers Using TBSCl-InCl3 as a Catalyst
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In the presence of a catalytic amount of t-butyldimethylsilyl chloride (TBSCl) and indium(III) chloride (InCl3), aldehydes smoothly react with t-butyldimethylsilyl enol ethers to afford the corresponding aldol adducts in good yields whereas acetals do not
- Mukaiyama, Teruaki,Ohno, Takashi,Han, Jeong Sik,Kobayashi, Shu
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p. 949 - 952
(2007/10/02)
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- Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of 2 and TMS-CN under Almost Neutral Conditions
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In the presence of catalytic amount of a transition metal compound such as 2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields.In the coexistence of catalytic amounts of Rh
- Soga, Tsunehiko,Takenoshita, Haruhiro,Yamada, Masaaki,Mukaiyama, Teruaki
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p. 3122 - 3131
(2007/10/02)
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- Efficient Activation of Acetals toward Nucleophiles with 2 Catalyst. New Method for the Preparation of Aldols from Acetals and Silyl Enol Ethers by the Combined Use of Catalytic Amounts of 2 and Trimethylsilyl Cyanide
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In the presence of a catalytic amount of 2, di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium, trimethylsilyl cyanide smoothly reacts with acetals derived from aliphatic, unsaturated and aromatic aldehydes to form the corresponding α-cyano derivativ
- Mukaiyama, Teruaki,Soga, Tsunehiko,Takenoshita, Haruhiro
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p. 1273 - 1276
(2007/10/02)
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