88946-47-8Relevant academic research and scientific papers
A Regiocontrolled and Stereocontrolled Synthesis of Allylsilanes from β-Silyl Enolates
Fleming, Ian,Gil, Salvador,Sarkar, Achintya K.,Schmidlin, Tibur
, p. 3351 - 3362 (2007/10/02)
The α-lithiated diphenylphosphine oxides 3 react with methyl iodide to give the phosphine oxides 4 and 5 in a ratio 3-4:1.The corresponding reaction with aldehydes gives all four diastereomeric alcohols 7-10, which are not suitable for the synthesis of allylsilanes by a Wittig-Horner reaction.The β-dimethyl(phenyl)silyl enolates 13-15 and 25-28 react with aldehydes to give aldol products with high diastereoselectivity.The benzyl and allyl ester groups can be cleaved from these aldols to give the acids 16-18 and 29-32.The acids, in turn, can be induced to undergo dec arboxylative elimination stereospecifically either in a syn or an anti sense to give the allylsilanes 19, 20, 23, 24, 33, 34 and 39-41.A similar series of reactions can be carried out with the β-trimethylsilyl enolates 45 and 46 giving the allylsilanes 49, 50, 53 and 54.
Cyclic Olefins by Anodic Oxidation of β-(Trimethylsilyl)carboxylic Acids. - β-(Trimethylsilyl)acrylic Acid Derivatives as Acetylene Equivalents in Diels-Alder Reactions
Hermeling, Dieter,Schaefer, Hans J.
, p. 1151 - 1158 (2007/10/02)
Trimethylsilyl-substituted dienophiles 1, 2, and 4 react with dienes 6-14 in 66-100percent yields to give β-trimethylsilyl-substituted carboxylic acids 15-25, some of which are hydrogenated to 26-31.These are decarboxylated-desilylated to cyclic olefins 35-47 by Non-Kolbe electrolysis in 45-91percent yields.The dienophiles 1, 2, and 4 are thus suitable acetylene equivalents for Diels-Alder reactions.
