120196-16-9Relevant academic research and scientific papers
The Regiochemistry and Stereochemistry of the Hydroboration of Allylsilanes
Fleming, Ian,Lawrence, Nicholas J.
, p. 3309 - 3326 (2007/10/02)
The hydroboration of a wide range of allylsilanes 3 and 5-21 is found to be generally regioselective for attachment of the boron to C-3 and hydrogen to C-2 of the allyl unit, and to be generally stereoselective in the sense 1, with attachment of the boron
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
STEREOCHEMISTRY IN THE HYDROBORATION OF ALLYLSILANES
Fleming, Ian,Lawrence, Nicholas, J.
, p. 2077 - 2080 (2007/10/02)
The hydroboration of allylsilanes is highly stereoselective in the sense (3 -> 4 and 6->7), especially with 9-BBN as the hydroborating reagent.The products can be converted stereospecifically into 1,3-diol derivatives (5 and 8).
REGIOCHEMISTRY IN THE HYDROBORATION OF ALLYLSILANES
Fleming, Ian,Lawrence, Nicholas, J.
, p. 2073 - 2076 (2007/10/02)
The hydroboration of most types of allylsilane is highly selective for the formation of the product having the silicon and boron in a 1,3 relationship when the hydroborating agent is 9-BBN.There is only a low degree of correlation between the difference in the chemical shifts of the trigonal carbon atoms on an alkene and the regioselectivity in hydroboration with either borane:THF or 9-BBN.
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.
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
