146565-66-4Relevant academic research and scientific papers
Enantioselective conjugate silyl additions to α,β-unsaturated aldehydes catalyzed by combination of transition metal and chiral amine catalysts
Ibrahem, Ismail,Santoro, Stefano,Himo, Fahmi,Cordova, Armando
, p. 245 - 252 (2011/04/18)
We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to α,β-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding β-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction can also generate a quaternary stereocenter with good enantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.
Remote asymmetric induction with vinylketene silyl N,O-acetal
Shirokawa, Shin-Ichi,Kamiyama, Masato,Nakamura, Tomoaki,Okada, Masakazu,Nakazaki, Atsuo,Hosokawa, Seijiro,Kobayashi, Susumu
, p. 13604 - 13605 (2007/10/03)
A highly regio- and diastereoselective TiCl4-mediated vinylogous Mukaiyama aldol reaction using the chiral vinylketene silyl N,O-acetal has been developed. The present vinylogous Mukaiyama aldol reaction provides a unique and effective means of
Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon
Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki
, p. 8211 - 8222 (2007/10/02)
Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.
Efficient Synthesis of Mugineic Acid, A Typical Phytosiderophore, Utilizing the Phenyl Group as the Carboxyl Synthon
Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki
, p. 7917 - 7920 (2007/10/02)
Stereoselective total synthesis of mugineic acid, a unique phytosiderophore from roots of barley, has been achieved from (2R,3R)- and (2S,3S)-2,3-epoxycinnamyl alcohols employing the phenyl group as the carboxyl synthon.
