156033-12-4Relevant academic research and scientific papers
The Ireland-Claisen rearrangement as a probe for the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group
Betson, Mark S.,Fleming, Ian
, p. 4005 - 4016 (2007/10/03)
The E- and Z-silyl enol ethers 4 derived from allyl 3-R-3-dimethyl(phenyl)silylpropanoate (R = Me, Pri and Ph) and the Z-silyl enol ethers 7 derived from 4-R-4-dimethyl(phenyl)silylbut-2-enyl acetate (R = Me and Pri) undergo Ireland-
Diastereoselectivity in the Preparation of β-Silyl Esters from αβ-Unsaturated Esters and Amides Attachhed to Chiral Auxiliaries
Fleming, Ian,Kindon, Nicolas D.
, p. 303 - 316 (2007/10/02)
The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides 1 of various known chiral auxiliaries, a-e, is diastereoselective.The sense of diastereoselectivity of silyl-cuprate addition to the esters 1b-d, 8 and 9 is different from established precedent based on carbon-cuprates, but is normal for silyl-cuprate addition to the amide 1a, the imines 1e and 21, and the oxazolidine 6.The chiral auxiliary e gives the best results of those tested, and the silicon-containing group can be removed from the chiral auxiliary using alkoxide ion in aprotic media, making available β-silyl esters 27-29 of high enantiomeric excess, with recovery of the chiral auxiliary 30.
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.
