G. Chelucci et al. / Tetrahedron: Asymmetry 17 (2006) 3163–3169
3169
8.56 (d, 1H, J = 4.2 Hz, major isomer), 8.55 (d, 1H,
References
J = 4.8 Hz, minor isomer), 7.64 (dt, 1H, J = 7.5, 1.5 Hz,
minor isomer), 7.57 (dt, 1H, J = 7.5, 1.5 Hz, major isomer),
7.46–7.23 (m, 5H, major isomer), 7.46–7.23 (m, 5H, minor
isomer), 7.41 (t, 1H, J = 7.5 Hz, minor isomer), 7.15 (ddd,
1H, J = 7.5, 6.0, 0.9 Hz, major isomer), 7.15 (ddd, 1H,
J = 7.5, 6.0, 0.9 Hz, minor isomer), 7.05 (d, 1H,
J = 8.1 Hz, major isomer), 5.77 (d, 1H, J = 2.7 Hz, major
isomer), 5.71 (d, 1H, J = 4.8 Hz, minor isomer), 5.64 (d,
1H, J = 3.0 Hz, major isomer), 4.85 (d, 1H, J = 4.8 Hz,
minor isomer), 1.27 (s, 9H, major isomer), 1.22 (s, 9H, min-
or isomer). Anal. Calcd for C16H20N2OS: C, 66.63; H, 6.99;
N, 9.71. Found: C, 66.54; H, 7.01; N, 9.74.
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4.6.10. (RS,R)- and (RS,S)-N-[Furan-2-yl(pyridin-2-yl)meth-
yl]-2-methylpropane-2-sulfinamide (10d). This compound
was obtained as a mixture of diastereomers. The spectra
data refer to the case in which the (RS,S)-diastereomer is
1
prevailing; chromatographic eluent: ethyl acetate; oil; H
NMR: d 8.58 (ddd, 1H, J = 4.8, 1.8, 0.9 Hz, major isomer),
8.58 (ddd, 1H, J = 4.8, 1.8, 0.9 Hz, minor isomer), 7.69 (td,
1H, J = 7.8, 1.8 Hz, minor isomer) 7.66 (td, 1H, J = 7.8,
1.8 Hz, major isomer), 7.41 (d, 1H, J = 7.8 Hz, minor iso-
mer), 7.38 (dd, 1H, J = 1.8, 0.6 Hz, major isomer) 7.26–
7.18 (m, 2H, major isomer), 7.26–7.18 (m, 2H, minor iso-
mer), 6.37–6.22 (m, 2H, major isomer), 6.37–6.22 (m, 3H,
minor isomer), 5.72 (d, 1H, J = 4.2 Hz, major isomer),
5.53 (d, 1H, J = 3.9 Hz, major isomer), 4.85 (d, 1H,
J = 6.0 Hz, minor isomer), 1.28 (s, 9H, major isomer),
1.22 (s, 9H, minor isomer). Anal. Calcd for C14H18N2O2S:
C, 60.41; H, 6.52; N, 10.06. Found: C, 60.33; H, 6.44; N,
10.03.
4.6.11. (RS,R)- and (RS,S)-N-[Pyridin-2-yl(thiophen-2-
(10e). This
yl)methyl]-2-methylpropane-2-sulfinamide
compound was obtained as a mixture of diastereomers.
The spectra data refer to the case in which the (RS,S)-diaste-
reomer is prevailing; chromatographic eluent: ethyl acetate;
oil; 1H NMR: d 8.58 (d, 1H, J = 4.8 Hz, major isomer), 8.58
(d, 1H, J = 4.8 Hz, minor isomer), 7.68 (dt, 1H, J = 7.8,
1.5 Hz, major isomer), 7.68 (dt, 1H, J = 7.5, 1.5 Hz, minor
isomer), 7.73–7.52 (m, 1H, minor isomer), 7.42 (d, 1H,
J = 7.8 Hz, major isomer), 7.28–7.16 (m, 2H, major iso-
mer), 7.28–7.16 (m, 2H, minor isomer), 7.05–7.01 (m, 2H,
major isomer) 7.00–6.90 (m, 1H, major isomer), 7.08–6.90
(m, 1H, minor isomer), 5.95 (d, 1H, J = 5.4 Hz, major iso-
mer), 5.91 (d, 1H, J = 3.9 Hz, minor isomer), 5.75 (d, 1H,
J = 3.9 Hz, minor isomer), 4.82 (d, 1H, J = 5.4 Hz, major
isomer), 1.30 (s, 9H, minor isomer), 1.23 (s, 9H, major iso-
mer). Anal. Calcd for C14H18N2OS2: C, 57.11; H, 6.16; N,
9.51. Found: C, 57.22; H, 6.18; N, 9.49.
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Financial support from MIUR (PRIN 2005035123-Regio-
and enantioselective reactions mediated by transition metal
catalysts for innovative processes in fine chemicals synthe-
sis) and from the University of Sassari is gratefully
acknowledged by G.C.