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Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions

Andrei Alexandrovich Vasil'ev 1
Andrei Alexandrovich Vasil'ev
Sergey Evgen'evich Lyubimov 2
Sergey Evgen'evich Lyubimov
Edward Prokof'evich Serebryakov 1
Edward Prokof'evich Serebryakov
Vadim Alexandrovich Davankov 2
Vadim Alexandrovich Davankov
Sergei Grigorievich Zlotin 1
Sergei Grigorievich Zlotin
Published 2011-12-29
CommunicationVolume 22, Issue 1, 39-40
7
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Vasil'ev A. A. et al. Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 39-40.
GOST all authors (up to 50) Copy
Vasil'ev A. A., Lyubimov S. E., Serebryakov E. P., Davankov V. A., Zlotin S. G. Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions // Mendeleev Communications. 2011. Vol. 22. No. 1. pp. 39-40.
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TY - JOUR
DO - 10.1016/j.mencom.2012.01.015
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.015
TI - Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions
T2 - Mendeleev Communications
AU - Vasil'ev, Andrei Alexandrovich
AU - Lyubimov, Sergey Evgen'evich
AU - Serebryakov, Edward Prokof'evich
AU - Davankov, Vadim Alexandrovich
AU - Zlotin, Sergei Grigorievich
PY - 2011
DA - 2011/12/29
PB - Mendeleev Communications
SP - 39-40
IS - 1
VL - 22
ER -
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@article{2011_Vasil'ev,
author = {Andrei Alexandrovich Vasil'ev and Sergey Evgen'evich Lyubimov and Edward Prokof'evich Serebryakov and Vadim Alexandrovich Davankov and Sergei Grigorievich Zlotin},
title = {Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions},
journal = {Mendeleev Communications},
year = {2011},
volume = {22},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.015},
number = {1},
pages = {39--40},
doi = {10.1016/j.mencom.2012.01.015}
}
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Vasil'ev, Andrei Alexandrovich, et al. “Asymmetric Tsuji–Trost substitution in 3-acetoxy-1,3-diphenylpropene under phase-transfer conditions.” Mendeleev Communications, vol. 22, no. 1, Dec. 2011, pp. 39-40. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2012.01.015.

Abstract

P*-Chiral diamidophosphite ligand-assisted Pd-catalyzed Tsuji–Trost reaction between dimethyl malonate and prochiral 3-acetoxy-1,3-diphenylpropene in organic solvents using potassium carbonate as the base affords the substitution product in quantitative yields and with enantioselectivities up to 99% ee.

References

2.
Asymmetric Transition Metal-Catalyzed Allylic Alkylations
Trost B.M., Van Vranken D.L.
Chemical Reviews, 1996
3.
Metal-Catalyzed Enantioselective Allylation in Asymmetric Synthesis
Lu Z., Ma S.
Angewandte Chemie - International Edition, 2008
4.
Vasil’ev A.A., Lyubimov S.E., Serebryakov E.P., Davankov V.A., Zlotin S.G.
Mendeleev Communications, 2009
5.
Pd-catalyzed allylation of CH acids under phase-transfer conditions
Vasil’ev A.A., Lyubimov S.E., Serebryakov E.P., Davankov V.A., Struchkova M.I., Zlotin S.G.
Russian Chemical Bulletin, 2010
6.
(a) S. A. Lebedev, L.F. Starosel'skaya and E. S. Petrov, Zh. Org. Khim., 1986, 22, 1565 [J. Org. Chem. USSR (Engl. Transl.), 1986, 22, 1410];
7.
(b) S. A. Lebedev, Yu. P. Leonova, S.S. Berestova and E. S. Petrov, Zh. Org. Khim., 1988, 24, 1112.[J. Org. Chem. USSR (Engl. Transl.), 1988, 24, 1005].
8.
The use of a new carboranylamidophosphite ligand in the asymmetric Pd-catalysed allylic alkylation in organic solvents and supercritical carbon dioxide
Lyubimov S.E., Kuchurov I.V., Vasil’ev A.A., Tyutyunov A.A., Kalinin V.N., Davankov V.A., Zlotin S.G.
Journal of Organometallic Chemistry, 2009
9.
Lyubimov S.E., Kuchurov I.V., Vasil’ev A.A., Zlotin S.G., Davankov V.A.
Mendeleev Communications, 2010
10.
P-Chiral Monodentate Diamidophosphites− New and Efficient Ligands for Palladium-Catalysed Asymmetric Allylic Substitution
Tsarev V., Lyubimov S., Shiryaev A., Zheglov S., Bondarev O., Davankov V., Kabro A., Moiseev S., Kalinin V., Gavrilov K.
European Journal of Organic Chemistry, 2004
11.
P*,N-Bidentate Amino Phosphoramidites: New Highly Effective Ligands for Pd-Catalysed Asymmetric Allylic Substitution
Gavrilov K., Tsarev V., Shiryaev A., Bondarev O., Lyubimov S., Benetsky E., Korlyukov A., Antipin M., Davankov V., Gais H.
European Journal of Inorganic Chemistry, 2004
12.
The use of an ionic liquid in asymmetric catalytic allylic amination
Lyubimov S.E., Davankov V.A., Gavrilov K.N.
Tetrahedron Letters, 2006
13.
Chiral cationic diamidophosphite: Novel effective ligand for Pd-catalysed enantioselective allylic substitution
Lyubimov S.E., Davankov V.A., Maksimova M.G., Petrovskii P.V., Gavrilov K.N.
Journal of Molecular Catalysis A Chemical, 2006
14.
Chiral Ionic Phosphites and Diamidophosphites: A Novel Group of Efficient Ligands for Asymmetric Catalysis
Gavrilov K., Lyubimov S., Bondarev O., Maksimova M., Zheglov S., Petrovskii P., Davankov V., Reetz M.
Advanced Synthesis and Catalysis, 2007
15.
MOP-Type Binaphthyl Phosphite and Diamidophosphite Ligands and Their Application in Catalytic Asymmetric Transformations
Gavrilov K., Lyubimov S., Zheglov S., Benetsky E., Petrovskii P., Rastorguev E., Grishina T., Davankov V.
Advanced Synthesis and Catalysis, 2007
16.
Diastereomeric P*-mono- and P*,P*-bidentate diamidophosphite ligands based on 1,4:3,6-dianhydro-d-mannitol in asymmetric metallocomplex catalysis
Gavrilov K.N., Zheglov S.V., Vologzhanin P.A., Rastorguev E.A., Shiryaev A.A., Maksimova M.G., Lyubimov S.E., Benetsky E.B., Safronov A.S., Petrovskii P.V., Davankov V.A., Schäffner B., Börner A.
Russian Chemical Bulletin, 2008
17.
A P∗-chiral bisdiamidophosphite ligand with a 1,4:3,6-dianhydro-d-mannite backbone and its application in asymmetric catalysis
Gavrilov K.N., Zheglov S.V., Vologzhanin P.A., Maksimova M.G., Safronov A.S., Lyubimov S.E., Davankov V.A., Schäffner B., Börner A.
Tetrahedron Letters, 2008
19.
Catalytic Asymmetric Alkylation in Water in the Presence of Surfactants
Sinou D., Rabeyrin C., Nguefack C.
Advanced Synthesis and Catalysis, 2003
21.
Practical Pd/C-mediated allylic substitution in water.
Felpin F., Landais Y.
Journal of Organic Chemistry, 2005