29843-69-4Relevant academic research and scientific papers
Organo[2-(hydroxymethyl)phenyl]dimethylsilanes as mild and reproducible agents for rhodium-catalyzed 1,4-addition reactions
Nakao, Yoshiaki,Chen, Jinshui,Imanaka, Hidekazu,Hiyama, Tamejiro,Ichikawa, Yoshitaka,Duan, Wei-Liang,Shintani, Ryo,Hayashi, Tamio
, p. 9137 - 9143 (2008/02/09)
Stable and reusable tetraorganosilicon reagents, alkenyl-, aryl-, and silyl[2-(hydroxymethyl)phenyl]-dimethylsilanes, undergo 1,4-addition reactions to α,β-unsaturated carbonyl acceptors under mild rhodium-catalysis. The reaction tolerates a diverse range of functional groups and is applicable to gram-scale synthesis. Use of a chiral diene ligand allows the achievement of the corresponding enantioselective transformations using the tetraorganosilicon reagents, providing the silicon-based approach to optically active ketones and substituted piperidones that serve as synthetic intermediates of pharmaceuticals. A rhodium alkoxide species is suggested to be responsible for a transmetalation step on the basis of the observed kinetic resolution of a racemic chiral phenylsilane in the enantioselective 1,4-addition reaction under the rhodium-chiral diene catalysis.
A Facile Synthesis of Bicycloalkan-1-ols. Evidence for Organosamarium Intermediates in the Samarium(II) Iodide Promoted Intramolecular Barbier-Type Reaction
Molander, Gary A.,McKie, Jeffrey A.
, p. 4112 - 4120 (2007/10/02)
Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicycloalkan-1-ols.Thus, a variety of 3-(ω-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic q
ORGANOMANGANESE (II) REAGENTS XVI: COPPER-CATALYZED 1,4-ADDITION OF ORGANOMANGANESE CHLORIDES TO CONJUGATED ENONES
Cahiez, Gerard,Alami, Mouad
, p. 3541 - 3544 (2007/10/02)
Copper-catalyzed conjugate addition of organomanganese chlorides to conjugated enones in THF, at 0 deg C, leads to the 1,4-addition products in high yields.The scope of the reaction is very large and the results are generally better than those obtained from organomagnesium compounds in the presence of a copper salts as well as from organocopper or cuprate reagents.Furthermore organomanganese chlorides are indisputably cheaper and more stable than the latter.
ORGANOMANGANESE (II) REAGENTS XI. A Study of their Reactions with Cyclic Conjugated Enones : Conjugate Addition and Reductive Dimerization
Cahiez, G.,Alami, M.
, p. 569 - 572 (2007/10/02)
The reaction of organomanganese reagents such as RMnX, R2Mn, R3MnLi and R3MnMgX with cyclohexenone has been studied.Two major pathways have been observed : conjugate addition and β reductive dimerization.Similar results have been obtained with organomagnesium compounds in presence of a catalytic amount of manganous salts.
