89881-82-3Relevant articles and documents
Diastereoselective free radical halogenation, azidation, and rearrangement of β-silyl Barton esters
Masterson, Douglas S.,Porter, Ned A.
, p. 4253 - 4256 (2007/10/03)
(equation presented) Barton esters of β-silylcarboxylic acids were decomposed by photolysis alone in organic solvents or in the presence of ethanesulfonyl azide or bromotrichloromethane. Products of the reaction, β-silylthiopyridyl ethers, β-silyl azides, or alkenes, were formed with significant control of stereochemistry.
Conjugate Addition of the Phenyldimethylsilyl Group to αβ-Unsaturated Carbonyl Compounds Using a Silylzincate in Place of the Silylcuprate
Crump, Roger A. N. C.,Fleming, Ian,Urch, Christopher J.
, p. 701 - 706 (2007/10/02)
Lithium phenyldimethylsilyl(dialkyl)zincates add to a number of αβ-unsaturated carbonyl compounds to give, in most cases, higher yields of the conjugate addition product than we had achieved with the corresponding silylcuprate.
The Diastereoselectivity of Electrophilic Attack on Trigonal Carbon Adjacent To a Stereogenic Centre: Diastereoselective Alkylation and Protonation of Open-chain Enolates Having a Stereogenic Centre Carrying a Silyl Group at the β Position
Crump, Roger A. N. C.,Fleming, Ian,Hill, John H. M.,Parker, David,Reddy, N. Laxma,Waterson, David
, p. 3277 - 3294 (2007/10/02)
The alkylation and protonation of enolates having a β-silyl group, prepared by conjugate addition of a silyl-cuprate reagent to enone systems, are almost always highly diastereoselective in the sense 3 in a wide variety of reactions.The effects of varying
A Synthesis of Allylsilanes in which the Silyl Group is at the More-substituted End of the Allyl Group
Fleming, Ian,Waterson, David
, p. 1809 - 1813 (2007/10/02)
The allylsilanes (8), (11), (18) - (20), and (26), have been made by a three-step sequence from αβ-unsaturated esters.The steps are conjugate addition of the phenyldimethylsilyl group, lithium aluminium hydride reduction, and selenium-mediated dehydration
Diastereoselectivity in the Alkylation of Enolates having an Adjacent Silyl Group
Bernhard, Werner,Fleming, Ian,Waterson, David
, p. 28 - 29 (2007/10/02)
The methylation of open-chain enolates having an adjacent silyl group is highly diastereoselective in favour of the isomer (2) having the silyl and methyl groups trans on the carbon chain; protonation of the corresponding enolate, already carrying the methyl group, gives the other diastereoisomer (3), but with somewhat lower diastereoselectivity.