117005-89-7Relevant academic research and scientific papers
Chiral silanes via asymmetric hydrosilylation with catalytic CuH
Lipshutz, Bruce H.,Tanaka, Naoki,Taft, Benjamin R.,Lee, Ching-Tien
, p. 1963 - 1966 (2007/10/03)
CuH-catalyzed asymmetric conjugate reduction of β-silyl-α, β-unsaturated esters has been developed. Using PMHS as a stoichiometric source of hydride and in situ generated CuH ligated by Solvias' JOSIPHOS analogue PPF-P(t-Bu)2 leads to highly enantioselective 1,4-reductions.
Conjugate additions of a simple monosilylcopper reagent with use of the CuI-DMS complex: Stereoselectivities and a dramatic impact by DMS
Dambacher, Jesse,Bergdahl, Mikael
, p. 580 - 589 (2007/10/03)
(Chemical Equation Presented) Conjugate additions utilizing the simple monosilylcuprate reagent Li[PhMe2SiCuI] to α,β-unsaturated carbonyl compounds are described. The presence of dimethyl sulfide (DMS), either as a component originating from t
Employing the simple monosilylcopper reagent, Li[PhMe2SiCuI], in 1,4-addition reactions
Dambacher, Jesse,Bergdahl, Mikael
, p. 144 - 145 (2007/10/03)
Conjugate addition reactions using the simple Li[PhMe2SiCuI] reagent to a variety of α,β-unsaturated carbonyl compounds is described; dimethyl sulfide from the purification of CuI plays a key role for very high yields as well as high stereosele
A synthesis of enantiomerically enriched propargyl silanes
Fleming, Ian,Mwaniki, Joseph M.
, p. 1237 - 1247 (2007/10/03)
Reduction of ethyl 3-methyl-, 3-isopropyl- and 3-n-pentyl-3-[dimethyl(phenyl)silyl]propanoates 4 with DIBAL to the aldehydes 5, enol trifluoromethanesulfonate (triflate) formation using trifluoromethanesulfonic (triflic) anhydride and 2,6-di-tert-butylpyridine, and elimination using LDA, gives the propargyl silanes 8. The esters 4 could also be prepared enantiomerically enriched (11), and the final products are the enantiomerically enriched propargyl (homochiral) silanes 14.
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.
Diastereoselectivity in the Preparation of β-Silylesters from αβ-Unsaturated Esters and Amides Attached to Chiral Auxiliaries
Fleming, Ian,Kindon, Nicholas D.
, p. 1177 - 1179 (2007/10/02)
The conjugate addition of the phenyldimethylsilyl-cuprate reagent to cinnamate and crotonate esters and amides of various known chiral auxiliaries is diastereoselective, making available β-silylesters of high enantiomeric excess; the sense of the diastereoselectivity is anomalously different from established precedent in the case of silyl-cuprate addition to the cinnamate ester (1, R = Ph, R* = d).
