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

doi:10.1016/j.mencom.2012.01.015

Mendeleev Communications

Volume 22, Issue 1, January–February 2012, Pages 39-40

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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 (9)

H. Kodama et al.
Tetrahedron: Asymmetry
(2000)
(a) B. M. Trost, Acc. Chem. Res., 1996, 29, 355; (b) B. M. Trost and D. L. Van Vranken, Chem. Rev., 1996, 96, 395; (c)...
(a) A. A. Vasil’ev, S.E. Lyubimov, E.P. Serebryakov, V.A. Davankov and S. G. Zlotin, Mendeleev Commun., 2009, 19, 103;...
(a) S. A. Lebedev, L.F. Starosel'skaya and E. S. Petrov, Zh. Org. Khim., 1986, 22, 1565 [J. Org. Chem. USSR (Engl....

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

Tetrahedron: Asymmetry