205752-81-4Relevant academic research and scientific papers
Enantioselective Synthesis of Chiral 3-Substituted-3-silylpropionic Esters via Rhodium/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
Zhang, Zongpeng,Han, Zhengyu,Gu, Guoxian,Dong, Xiu-Qin,Zhang, Xumu
, p. 2585 - 2589 (2017/08/16)
We have successfully developed the asymmetric hydrogenation of β-silyl-α,β-unsaturated esters to prepare chiral 3-substituted-3-silylpropionic ester products catalyzed by rhodium/bisphosphine-thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)-3-hydroxy-3-phenylpropanoate or (R)-3-[dimethyl(phenyl)silyl]-3-phenylpropanoic acid. (Figure presented.).
A conjugate reduction pathway to chiral silanes using CuH
Lipshutz, Bruce H.,Lee, Ching-Tien,Taft, Benjamin R.
, p. 3257 - 3260 (2008/09/19)
Experimental details concerning asymmetric 1,4-reduction of β-silylated-β,β-disubstituted enoates catalyzed by CuH are described. High yields and enantiomeric excesses are to be expected when Solvias' JOSIPHOS bis-phosphine PPF-P(t-Bu)2 is used as a non-racemic ligand. Georg Thieme Verlag Stuttgart.
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.
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.
