Asymmetric allylation
Russ. Chem. Bull., Int. Ed., Vol. 70, No. 2, February, 2021
339
determined by HPLC on a Daicel Chiralcel OD-H chiral station-
15. R. Murakami, K. Sano, T. Iwai, T. Taniguchi, K. Monde,
i
–1
ary phase (eluent C H —Pr OH (99 : 1), 0.3 mL min , 254 nm,
M. Sawamura, Angew. Chem., Int. Ed., 2018, 57, 9465.
16. K. N. Gavrilov, I. S. Mikhel, S. V. Zheglov, V. K. Gavrilov,
I. V. Chuchelkin, I. D. Firsin, K. P. Birin, I. S. Pytskii, K. A.
Paseshnichenko, V. A. Tafeenko, V. V. Chernyshev, A. A.
Shiryaev, Org. Chem. Front., 2019, 6, 1637.
6
14
t(R) = 28.0 min, t(S) = 29.3 min).
Asymmetric amination of (E)-1,3-diphenylallyl acetate (6)
with pyrrolidine. A solution of [Pd(All)Cl] (0.0019 g, 0.005 mmol)
2
and ligand 5 (0.0037 g, 0.005 mmol, or 0.0073 g, 0.01 mmol, or
0
.0146 g, 0.02 mmol) in the corresponding solvent (5 mL) was
17. K. N. Gavrilov, S. V. Zheglov, V. K. Gavrilov, I. D. Firsin,
M. G. Maksimova, Russ. Chem. Bull., 2019, 68, 1376.
18. B. M. Trost, A. H. Shinde, Y. Wang, Z. Zuo, C. Min, ACS
Catal., 2020, 10, 1969.
stirred for 40 min. (E)-1,3-Diphenylallyl acetate (0.1 mL,
0
1
.5 mmol) was added and the solution was stirred for another
5 min, then freshly distilled pyrrolidine (0.12 mL, 1.5 mmol)
was added. The reaction mixture was stirred for 48 h, diluted
with hexane (5 mL), and filtered through a short layer of SiO2.
The solvents were evaporated under reduced pressure (40 Torr),
the residue was vacuum dried (10 Torr). The conversion of sub-
strate 6 and the enantiomeric excess of product 8 were determined
by HPLC on a Daicel Chiralcel OD-H chiral stationary phase
19. Q.-L. Zhou, Privileged Chiral Ligands and Catalysts, Ed.
Q.-L. Zhou, Wiley—VCH, Weinheim, 2011, 462 pp.
20. S. Shaw, J. D. White, Chem. Rev., 2019, 119, 9381.
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Asymmetric Catalysis, Ed. A. Börner, Wiley—VCH, Weinheim,
2008, Vol. 2, 529.
i
–1
(
eluent C H —Pr OH—HNEt (200 : 1 : 0.1), 0.9 mL min
,
22. M. T. Reetz, H. Oka, R. Goddard, Synthesis, 2003, 1809.
23. K. V. L. Crepy, T. Imamoto, Adv. Synth. Catal., 2003, 345, 79.
6
14
2
2
54 nm, t(R) = 5.0 min, t(S) = 6.1 min).
2
4. A. Grabulosa, P-Stereogenic Ligands in Enantioselective
Catalysis, Ed. A. Grabulosa, Royal Society of Chemistry,
Cambridge, 2011, 501 pp.
5. H. Fernandez-Perez, P. Etayo, A. Panossian, A. Vidal-Ferran,
Chem. Rev., 2011, 111, 2119.
This work was financially supported by the Russian
Foundation for Basic Research (Project No. 1843623001
r_mol_а).
2
2
2
2
6. B. M. Trost, Org. Process Res. Dev., 2012, 16, 185.
7. Z. Lu, S. Ma, Angew. Chem., Int. Ed., 2008, 47, 258.
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Received June 4, 2020;
in revised form October 22, 2020;
accepted October 27, 2020