167990-19-4Relevant academic research and scientific papers
DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones
Zhang, Yuhua,Li, Chao-Jun
, p. 4242 - 4243 (2007/10/03)
A direct Cross-Dehydrogenative-Coupling (CDC) between benzyl ethers and simple ketones was developed without using any metal catalyst. By using DDQ, various benzyl ethers and simples ketones were coupled together directly to form β-alkoxyl ketones efficie
Efficient One-Step Aldol-Type Reaction of Ketones with Acetals and Ketals Mediated by Dibutylboron Triflate/ Diisopropylethyl Amine
Li, Lian-Sheng,Das, Sanjib,Sinha, Subhash C.
, p. 127 - 130 (2007/10/03)
(Equation presented) A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of β-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu2BOTf and i-Pr2NEt affording the products in high yields. Formation of the two possible diastereoisomers of the β-alkoxy ketones from the chiral acetals shows that the condensation takes place by an SN1 mechanism, involving prior opening of the acetal to an oxonium ion.
Tris(pentafluorophenyl)boron as an Efficient, Air Stable, and Water Tolerant Lewis Acid Catalyst
Ishihara, Kazuaki,Hanaki, Naoyuki,Funahashi, Miyuki,Miyata, Mayumi,Yamamoto, Hisashi
, p. 1721 - 1730 (2007/10/02)
Tris(pentafluorophenyl)boron is an efficient, air stable, and water tolerant Lewis acid catalyst for the aldol-type and Michael reactions of silyl enol ethers with carbonyl compounds or other electrophiles (trimethyl orthoformate, dimethal acetal, and chloromethyl methyl ether), the allylation reaction of allylsilanes with aldehydes, and the Diels-Alder reaction of dienes with α,β-unsaturated-aldehydes.A solution of formaldehyde in water is applicable as an electrophile.Also, the aldol-type reaction of ketene silyl acetals with aromatic or aliphatic imines is successfully carried out using the same catalyst.
TRIMETHYLSILYL TRIFLATE CATALYZED ALDOL-TYPE REACTION OF ENOL SILYL ETHERS AND ACETALS OR RELATED COMPOUNDS
Murata, Shizuaki,Suzuki, Chikusa,Noyori, Ryoji
, p. 4259 - 4276 (2007/10/02)
Trimethylsilyl triflate with or without added hindered tertiary amines catalyzes directed condensation of enol trimethylsilyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds.R
An Essentially Mild and Efficient Catalyst System for the Activation of Carbonyl Compounds and Their Derivatives. The Combined Use of Trimethylsilyl Chloride and Tin(II) Chloride
Iwasawa, Nobuharu,Mukaiyama, Teruaki
, p. 463 - 466 (2007/10/02)
An essentially mild and efficient catalyst system, the combined use of trimethylsilyl chloride and tin(II) chloride, is effectively employed for the activation of acetals, aldehydes, orthoesters, and α,β-unsaturated ketones to accomplish the reaction with
ALDOL-TYPE REACTIONS BETWEEN TRIMETHYLSILYL ENOL ETHERS AND ACETALS WITH THE AID OF RHODIUM COMPLEX
Sato, Susumu,Matsuda, Isamu,Izum, Yusuke
, p. 6657 - 6660 (2007/10/02)
Aldol type reactions of trimethylsilyl enol ethers with acetals, ketals and orthoesters are successfully performed with the aid of a catalytic amount of rhodium complex Rh4(CO)12 or (Rh(COD)(DPPB))(1+)*ClO4(1-), under neutral conditions.
