M. Dubois et al. / Tetrahedron 68 (2012) 7140e7147
7147
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6034e6038.
4.7.1. (S)-3-Phenyl-1,2,3,4-tetrahydroisoquinoline [(S)-2a]. Pale yel-
low oil, ½a 2D0
ꢃ
ꢀ125.5 (c 0.48, CH2Cl2); lit.:24 (R)-enantiomer ½a 2D0
ꢃ
þ125.0 (c 0.55, CH2Cl2). Spectral data were identical to those
already published.24
7. (a) Vicario, J. L.; Badia, D.; Dominguez, E.; Carrillo, L. Tetrahedron: Asymmetry
2000, 11, 1227e1237; (b) Vicario, J. L.; Badia, D.; Dominguez, E.; Crespo, A.;
Carrillo, L. Tetrahedron: Asymmetry 1999, 10, 1947e1959; (c) Ishikawa, T.; Ishii,
H. Heterocycles 1999, 50, 627e639; (d) Carrillo, L.; Badia, D.; Dominguez, E.;
Vicario, J. L.; Tellitu, I. J. Org. Chem. 1997, 62, 6716e6721; (e) Meyers, A. I. Tet-
4.7.2. (S)-3-(4-Methoxyphenyl)-1,2,3,4-tetrahydroisoquinoline [(S)-
2d]. Pale yellow oil, ½a D20
ꢃ
ꢀ118.8 (c 1.05, CHCl3); lit.:13 (R)-enan-
tiomer ½a 2D0
þ119.1 (c 1.39, CHCl3). Spectral data were identical to
ꢃ
€
rahedron 1992, 48, 2589e2612; (f) Gozler, B. In; Brossi, A., Ed.; The Alkaloids;
Academic: San Diego, 1987; Vol. 31, pp 317e388; (g) Bhakuni, D. S.; Jain, S. In;
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New York, NY, 1979; Vol. 17, pp 385e544.
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Collect. Czech. Chem. Commun. 1983, 48, 1447e1464; (b) Cushman, M.; Choong,
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M.; Tomlinson, H. H. J. Org. Chem. 1978, 43, 2852e2855; (d) Ito, K.; Furukawa,
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Maeno, K.; Seki, N. PCT Int. Appl., WO 2008146774, 2008; Chem. Abstr. 2008,
150, 20012.
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Ross, G.; Skobeleva, N.; Weber, L.; Holak, T. A. ChemMedChem 2008, 3,
1118e1128.
11. (a) Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1e314; (b) Snieckus, V. Chem.
Rev. 1990, 90, 879e933; (c) Clark, R. D.; Jahangir, A. J. Org. Chem. 1989, 54,
1174e1178; (d) Jahangir, A.; Fisher, L. E.; Clark, R. D.; Muchowski, J. M. J. Org.
Chem. 1989, 54, 2992e2996; (e) Clark, R. D.; Jahangir, A. J. Org. Chem. 1988, 53,
2378e2381; (f) Clark, R. D.; Jahangir, A. J. Org. Chem. 1987, 52, 5378e5382.
12. (a) Davis, F. A.; Chao, B.; Andemichael, Y. W.; Mohanty, P. K.; Fang, T.; Burns, D.
M.; Rao, A.; Szewczyk, J. M. Heteroat. Chem. 2002, 13, 486e492; (b) Davis, F. A.;
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those already published for the enantioenriched (ee 92%) (R)-2d.24
4.7.3. (S)-3,1,3-Benzodioxol-5-yl-1,2,3,4-tetrahydroisoquinoline [(S)-
2e]. Pale yellow oil, ½a D20
ꢃ
ꢀ115.5 (c 0.97, CHCl3). IR (neat)
n
¼2897,
1485, 1434, 1230 cmꢀ1. 1H NMR (300 MHz, CDCl3)
d
¼1.88 (br s, 1H),
2.90 (d, J¼7.2 Hz, 2H), 3.90 (t, J¼7.2 Hz, 1H), 4.12 (d, J¼15.5 Hz, 1H),
4.22 (d, J¼15.5 Hz, 1H), 5.91 (s, 2H), 6.78 (d, J¼8.0 Hz, 1H), 6.87 (dd,
J¼1.5, 8.0 Hz, 1H), 6.94 (d, J¼1.5 Hz, 1H), 7.01e7.18 (m, 4H) ppm. 13C
NMR (75 MHz, CDCl3):
d
¼37.9 (CH2), 49.3 (CH2), 58.4 (CH), 101.0
(CH2), 107.1 (CH), 108.2 (CH), 119.7 (CH), 125.9 (CH), 126.2 (CH),
126.3 (CH), 129.1 (CH), 134.9 (C), 135.0 (C), 138.5 (C), 146.7 (C), 147.8
(C) ppm. Anal. Calcd for C16H15NO2: C, 75.87; H, 5.97; N, 5.53%.
Found: C, 76.04; H, 6.12; N, 5.77%.
Acknowledgements
This research was supported by the CNRS and by MENESR.
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