120881-25-6Relevant articles and documents
Palladium-catalyzed silylene-1,3-diene [4 + 1] cycloaddition with use of (aminosilyl)boronic esters as synthetic equivalents of silylene
Ohmura, Toshimichi,Masuda, Kohei,Takase, Ichiro,Suginome, Michinori
supporting information; experimental part, p. 16624 - 16625 (2010/02/16)
(Chemical Equation Presented) Silylboronic esters bearing a dialkylamino group on the silicon atoms reacted with 1,3-dienes in the presence of a palladium catalyst to give silacyclopent-3-enes (i.e., 2,5-dihydrosiloles) in high yields via efficient silyle
Chemistry of Substituted (2-Butene-1,4-diyl)magnesium: A Facile Approach to Complex Carbocycles, Functionalized Ketones and Alcohols, and Silicon-Containing Heterocycles
Rieke, Reuben D.,Xiong, Heping
, p. 3109 - 3118 (2007/10/02)
Highly reactive magnesium reacts with a wide variety of substituted 1,3-dienes to give the corresponding substituted (2-butene-1,4-diyl)magnesium complexes.Reactions of symmetrical (2-butene-1,4-diyl)magnesium with α,ω-alkylene dihalides form three-, four-, five-, and six-membered carbocycles.Significantly, the cyclizations are always stereospecific and completely regioselective.Depending on the initial 1,3-diene and specific electrophiles, uncyclized products can be obtained.Stepwise reactions of (2,3-dimethyl-2-butene-1,4-diyl)magnesium with two different electrophiles afford polyfunctionalized ketones with the generation of a quaternary center.Formal 1,2-additions can be effected in this manner.Substituted five- and six-membered cyclic ketones can also be synthesized in one step by this approach.Treatment of unsymmetrical (2-butene-1,4-diyl)magnesium complexes with triorganosilyl chlorides followed by cyclohexanone results in additions across a terminal double bond with high regioselectivity.Silicon-containing heterocycles or spiro compounds can be readily synthesized by using the bis-Grignard reagents.
Facile Formation of Substituted 2-Butene-1,4-diylmagnesium Using Highly Reactive Magnesium: A Simple Approach to Complex Carbocycles and Functionalized Ketones
Xiong, Heping,Rieke, Reuben D.
, p. 3247 - 3249 (2007/10/02)
Substituted 2-butene-1,4-diylmagnesium compounds are readily prepared using highly reactive magnesium.Reactions with organodihalides yield 4-, 5-, and 6-membered carbocycles.In some cases, the initial monoalkylated intermediates can be reacted with other electrophiles.Polyfunctionalized ketones can be prepared in this manner.Depending on the initial 1,3-diene and by the proper choice of electrophiles, either 1,2-, 1,4-, or 2,1-additions may be observed.
