74209-73-7Relevant academic research and scientific papers
Reaction of acetals with various carbon nucleophiles under non-acidic conditions: C-C bond formation via a pyridinium-type salt
Fujioka, Hiromichi,Yahata, Kenzo,Hamada, Tomohito,Kubo, Ozora,Okitsu, Takashi,Sawama, Yoshinari,Ohnaka, Takuya,Maegawa, Tomohiro,Kita, Yasuyuki
, p. 367 - 373 (2012/05/05)
Mild substitution reactions of acetals with carbon nucleophiles via the pyridinium-type salts generated by the treatment of acetals with TESOTf-2,4,6-collidine or 2,2′-bipyridyl have been developed. Various carbon nucleophiles, such as organocuprates, sil
Cationic iridium complex is a new and efficient Lewis acid catalyst for aldol and Mannich reactions
Onodera, Gen,Toeda, Takayuki,Toda, Nou-No,Shibagishi, Daigo,Takeuchi, Ryo
experimental part, p. 9021 - 9031 (2011/01/04)
A cationic iridium complex [Ir(cod)2]SbF6 was found to be a new and efficient Lewis acid catalyst for Mukaiyama aldol and Mannich reactions. Aldehydes react smoothly with silyl enol ethers to give β-siloxy ketones in the presence of 0.5 mol % of [Ir(cod)2]SbF6. The reaction of N-alkyl arylaldimines with ketene silyl acetals in the presence of 5 mol % [Ir(cod)2]SbF6/P(OPh)3 gave β-amino esters. After Mannich reaction was complete, stirring of the reaction mixture for 24 h led to cyclization to give β-lactam. The reaction of N-aryl benzaldimine with silyl enol ether derived from acetophenone gave a tetrahydroquinoline derivative as a single diastereomer.
Lewis acid catalyst free electrophilic alkylation of silicon-capped π donors in 1,1,1,3,3,3-hexafluoro-2-propanol
Ratnikov, Maxim O.,Tumanov, Vasily V.,Smit, William A.
supporting information; experimental part, p. 9739 - 9742 (2009/05/30)
(Figure Presented) A credit to donation: A diverse range of electrophilic addition reactions, conventionally carried out using Lewis acid catalysts, have been performed in electrophilic media without acidic reagents. 1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) acts as an efficient hydrogen-bond donor and highly polar solvent for a wide range of substrates in reactions with Si-capped π donors.
Selective aldol reactions of acetals on mesoporous silica catalyst
Ishitani, Haruro,Iwamoto, Masakazu
, p. 299 - 301 (2007/10/03)
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
Carbon-carbon bond forming reactions by using bistrifluoromethanesulfonimide
Cossy,Lutz,Alauze,Meyer
, p. 45 - 48 (2007/10/03)
Bistrifluoromethanesulfonimide has been used to catalyze C-C bond forming reactions such as Friedel-Crafts, Mukaiyama, 1,2-addition and 1,4-addition as well as C-glycosidation reactions.
Iridium-catalyzed crossed aldol coupling and a new concept to form an Ir-Si species
Matsuda, Isamu,Hasegawa, Yuki,Makino, Tatsuya,Itoh, Kenji
, p. 1405 - 1408 (2007/10/03)
[Ir(COD)(PPh3)2]X (X=PF6, ClO4, and OTf) activated by H2 molecule catalyzes Mukaiyama-type aldol coupling between enoxysilanes and acetals or aldehydes. An Ir-Si species formed in the first stage of t
Bismuth(III) Triflate: A Water-Stable Equivalent of Trimethylsilyl Triflate for the Catalysis of Mukaiyama Aldol Reactions
Roux, C. Le,Ciliberti, L.,Laurent-Robert, H.,Laporterie, A.,Dubac, J.
, p. 1249 - 1251 (2007/10/03)
Bismuth tris-trifluoromethanesulfonate (1) has been found to be an efficient catalyst for the Mukaiyama aldol-type reactions.The catalytic activity of this catalyst is higher than the one previously reported for the rare earth triflates M(OTf)3 (M = Sc, L
Pyrylium salt promoted substitution reactions of acetals with various silylated nucleophiles
Kamata, Masaki,Nagai, Satoshi,Kato, Mitsuaki,Hasegawa, Eietsu
, p. 7779 - 7782 (2007/10/03)
Catalytic amounts of triarylpyrylium salts photochemically and thermally promoted the substitution reactions of dimethyl acetals with silylated nucleophiles.
Chemoselective aldol type condensation of silyl enol ethers and acetals in 5 mol dm-3 lithium perchlorate-diethyl ether
Saraswathy, V. Geetha,Sankararaman, S.
, p. 29 - 32 (2007/10/03)
Acetals are efficiently and chemoselectively converted into the corresponding aldol ethers upon treatment with 1-trimethylsilyloxycyclohexene 2 in 5 mol dm-3 lithium perchlorate-diethyl ether (LPDE) at ambient temperature with moderate diastereoselectivity, whereas under the same conditions aldehydes and ketals fail to react with 2.The present method allows the acetal substitution to be carried out under neutral reaction and work up conditions.A mechanism involving the formation of an oxocarbenium ion intermediate from the acetal followed by nucleophilic addition of the silyl enol ether is proposed.The observed chemoselectivity is attributed to the mild Lewis acidity of the lithium ion in diethyl ether.
Aminium salt promoted catalytic substitution reactions of acetals with silylated nucleophiles
Kamata, Masaki,Yokoyama, Yukiko,Karasawa, Natsuko,Kato, Mitsuaki,Hasegawa, Eietsu
, p. 3483 - 3486 (2007/10/03)
A catalytic amount of tris(p-bromophenyl)aminium hexachloroantimonate promoted the substitution reactions of dimethylacetals with various silylated nucleophiles through an electron transfer mechanism. Silyl compounds include silyl enol ether, ketene silyl
