82105-27-9Relevant academic research and scientific papers
TiCl4-n-Bu4NX (X = I, Br, and Cl) combination-induced coupling of α,β-unsaturated ketones with aldehydes
Han,Uehira,Shinokubo,Oshima
, p. 7854 - 7857 (2001)
A three-component coupling reaction between vinyl ketones, aldehydes, and halides has been developed with TiCl4-n-Bu4NX combined reagents, Treatment of vinyl ketones with a TiCl4-n-Bu4NI combination followed by an addition of a variety of aldehydes provides syn-α-iodomethyl-β-hydroxy ketones with high stereoselectivity. Methyltriphenylphosphonium iodide as well as n-Bu4NI acts efficiently as a halide source. The combination of TiCl4-n-Bu4NBr provides the corresponding bromo compounds in good yields. syn-α- Chloromethyl-β-hydroxy ketones are obtained with the TiCl4-n-Bu4NCl combination. A competitive experiment reveals that the order of relative reactivity of the combinations is TiCl4-n-Bu4NI > TiCl4-n-Bu4NBr > TiCl4-n-Bu4NCl.
Novel Reactive Silyl Enolates. Highly Stereoselective Aldol and Michael Reactions without Catalysts
Kobayashi, Shu,Nishio, Koichi
, p. 2647 - 2649 (2007/10/02)
Novel silyl enolates, prepared in situ from ketones and dimethylsilyl ditriflate (Me2Si(OTf)2) in the presence of a tertiary amine, reacted smoothly with electrophiles such as aldehydes, acetals, or α,β-unsaturated ketones without catalyst at -78 deg C to
Reaction of α-Halogeno Ketones with Carbonyl Compounds Promoted by CeI3, CeCl3-NaI,or CeCl3-SnCl2
Fukuzawa, Shin-ichi,Tsuruta, Takuya,Fujinami, Tatsuo,Sakai, Shizuyoshi
, p. 1473 - 1478 (2007/10/02)
Reaction of α-halogeno ketones with aldehydes in the presence of CeI3 in tetrahydrofuran is found to give α,β-unsaturated ketones in excellent yields under mild conditions.In contrast, treatment of α-halogeno ketones and carbonyl compounds with CeCl3-NaI or CeCl3-SnCl2 affords β-hydroxy ketones in good yields.It is assumed that these reactions proceed via cerium enolates.The combined reagents, however, cannot be applied to a Reformatsky-type reaction.Regiospecific and aldehyde chemoselective aldol synthesis are also described.
SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS
Mukaiyama, Teruaki,Iwasawa, Nobuharu,Stevens, Rodney W.,Haga, Toru
, p. 1381 - 1390 (2007/10/02)
A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia
A NEW ALDOL REACTION VIA CERIUM ENOLATES
Imamoto, Tsuneo,Kusumoto, Tetsuo,Yokoyama, Masataka
, p. 5233 - 5236 (2007/10/02)
Cerium enolates formed from cerium (III) chloride and lithium enolates undergo aldol reaction with ketones or sterically crowded aldehydes to afford the corresponding β-hydroxyketones in high yields.
A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN
Harada, Taira,Mukayiama, Teruaki
, p. 467 - 470 (2007/10/02)
Tin(II) enolates, generated in situ by the oxidative addition of α-bromoketones to metallic tin, react with a variety of carbonyl compounds under mild conditions to give the corresponding aldols in good yields.In the case of reactions of the enolate resul
STANNOUS TRIFLATE: A FACILE CROSS-ALDOL REACTION BETWEEN TWO KETONES VIA DIVALENT TIN ENOLATES
Stevens, Rodney W.,Iwasawa, Nobuharu,Mukaiyama, Teruaki
, p. 1459 - 1462 (2007/10/02)
Divalent tin enolates, formed from stannous triflate and ketones, react with a second ketone under mild conditions to afford the corresponding cross-aldol products in good to excellent yields.In the case of the cross-coupling with aromatic ketone, enhance
