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M. Stankevic et al. / Tetrahedron 72 (2016) 810e824
820
70 eV) m/z¼217 (14), 216 (100), 215 (41), 169 (30), 139 (10), 92 (8),
as a mixture of 15e, 15f, 15g and 16d. The same compound was
prepared from t-butyl(p-tolyl)phosphine oxide 19 through
palladium-catalyzed coupling with 3-bromoanizole followed by
reaction with t-BuLi. Colorless sticky oil; Rf (CH3Cl) 0.06; dH
(500 MHz, CDCl3) 1.15 (9H, d, J 15.5 Hz), 2.46 (3H, s), 4.02 (3H, s),
7.10e7.14 (1H, m), 7.17e7.20 (1H, m), 7.35e7.40 (1H, m), 7.41e7.45
(1H, m), 7.68e7.72 (1H, m), 8.18e8.21 (1H, m); dC (126 MHz, CDCl3)
22.1, 23.9, 32.8 (d, J 70.8 Hz), 55.4, 115.5 (d, J 1.9 Hz), 122.0 (d, J
9.1 Hz), 126.7 (d, J 98.1 Hz), 127.2 (d, J 10.0 Hz), 128.4 (d, J 10.9 Hz),
129.6 (d, J 9.1 Hz), 129.7 (d, J 20.0 Hz), 129.8 (d, J 11.8 Hz), 133.0 (d, J
93.6 Hz),141.9 (d, J 20.0 Hz),143.4 (d, J 1.8 Hz),156.7 (d, J 12.7 Hz); dP
(202 MHz, CDCl3) 53.40; GC tR¼12.64 min; GCeMS (EI, 70 eV) m/
z¼300 (13, Mþ), 245 (16), 244 (100), 243 (20), 229 (12), 213 (6), 200
(9), 182 (9), 171 (7%).
91 (28), 77 (10), 65 (14), 47 (25%).
4.1.34. m-Anisyl(t-butyl)phenylphosphine oxide (15f). This com-
pound was prepared according to general procedure (Method A)
from m-anisylphenyl-p-tolylphosphine oxide (14e) (0.161 g,
0.499 mmol) and tert-butyllithium (0.588 mL, 0.999 mmol, 1.7 M
solution in pentane): yield 0.001 g (1%). Isolated as a mixture of 15e,
15g, 16d and 16e. The same compound was prepared from t-
butylphenylphosphine oxide 18 through palladium-catalyzed
coupling with 3-bromoanizole. Yellow oil; Rf (CH3Cl) 0.13; dH
(500 MHz, CDCl3) 1.18 (9H, d, J 15.1 Hz), 3.75 (3H, s), 6.96e6.99 (1H,
m), 7.29e7.34 (1H, m), 7.37e7.46 (4H, m), 7.46e7.50 (1H, m),
7.86e7.91 (2H, m); dC (126 MHz, CDCl3) 25.0, 33.7 (d, J 70.8 Hz),
55.2, 117.2 (d, J 2.7 Hz), 117.4 (d, J 8.2 Hz), 123.9 (d, J 8.2 Hz), 128.0 (d,
J 10.9 Hz), 129.1 (d, J 12.7 Hz), 130.9 (d, J 90.8 Hz), 131.3 (d, J 2.7 Hz),
131.9 (d, J 8.2 Hz), 132.3 (d, J 89.9 Hz), 159.2 (d, J 13.6 Hz); dP
(202 MHz, CDCl3) 38.79; GC tR¼14.88 min; GCeMS (EI, 70 eV) m/
z¼288 (3, Mþ), 233 (15), 232 (100), 231 (34), 230 (16), 229 (10), 185
(19), 170 (12), 108 (24), 92 (11), 78 (12), 77 (34), 57 (10), 51 (10), 47
(20%).
4.1.38. o-Anisylphenyl(2-tert-butyl-1,2-dihydronaphth-1-yl)phos-
phine oxide (15h). This compound was prepared according to
general procedure (Method A) from o-anisyl-1-naphthyl-
phenylphosphine oxide (14f) (0.179 g, 0.499 mmol) and tert-
butyllithium (0.588 mL, 0.999 mmol, 1.7 M solution in pentane):
yield of two diastereomers (dr¼61:39) 0.054 g (26%). Isolated as
a mixture of diastereomers.
4.1.35. m-Anisyl(t-butyl)(p-tolyl)phosphine oxide (15g). This com-
pound was prepared according to general procedure (Method A)
from m-anisylphenyl-p-tolylphosphine oxide (14e) (0.161 g,
0.499 mmol) and tert-butyllithium (0.588 mL, 0.999 mmol, 1.7 M
solution in pentane): yield 0.009 g (6%); colorless oil. Isolated as
a mixture of 15e, 15f, 16d and 16e. The same compound was pre-
pared from t-butyl(p-tolyl)phosphine oxide 19 through palladium-
catalyzed coupling with 3-bromoanizole. Yellow oil; Rf (CH3Cl) 0.13;
dH (500 MHz, CDCl3) 1.20 (9H, d, J 14.8 Hz), 2.34 (3H, s), 3.79 (3H, s),
6.98e7.01 (1H, m), 7.22e7.26 (2H, m), 7.31e7.36 (1H, m), 7.42e7.46
(1H, m), 7.48e7.52 (1H, m), 7.78e7.83 (2H, m); dC (126 MHz, CDCl3)
21.3, 25.1, 33.8 (d, J 70.8 Hz), 55.2, 117.2 (d, J 2.7 Hz), 117.3 (d, J
9.1 Hz), 123.9 (d, J 8.2 Hz), 127.6 (d, J 92.6 Hz), 128.9 (d, J 10.9 Hz),
129.1 (d, J 12.7 Hz), 132.0 (d, J 8.2 Hz), 132.7 (d, J 89.0 Hz), 141.7 (d, J
2.7 Hz), 159.2 (d, J 13.6 Hz); dP (202 MHz, CDCl3) 39.01; GC
tR¼11.39 min; GCeMS (EI, 70 eV) m/z¼302 (3, Mþ), 247 (15), 246
(100), 245 (55), 199 (21), 184 (9), 155 (6), 152 (6), 139 (10), 108 (16),
92 (13), 91 (20), 78 (9), 77 (19), 65 (11), 57 (8), 47 (15%).
Major Diastereomer: Rf (CH3Cl) 0.15; dH (500 MHz, CDCl3) 0.81
(9H, s), 2.76 (1H, dd, J 6.0, 20.8 Hz), 4.06 (3H, s), 4.58 (1H, d, J
19.2 Hz), 5.73 (1H, dd, J 6.3,10.1 Hz), 6.23 (1H, d, J 9.8 Hz), 6.50e6.53
(1H, m), 6.76e6.81 (1H, m), 6.89e8.10 (11H, m); dC (126 MHz,
CDCl3) 26.9, 36.6 (d, J 15.4 Hz), 40.6 (d, J 63.6 Hz), 42.0 (d, J 2.7 Hz),
55.6, 111.0 (d, J 7.3 Hz), 121.0 (d, J 10.9 Hz), 126.1 (d, J 4.5 Hz), 126.5
(d, J 3.6 Hz), 127.0 (d, J 3.6 Hz), 127.1 (d, J 11.8 Hz), 127.6 (d, J 2.7 Hz),
128.4 (d, J 1.8 Hz), 131.1 (d, J 2.7 Hz), 132.6 (d, J 8.2 Hz), 133.8 (d, J
1.8 Hz), 135.5 (d, J 6.4 Hz), 160.5 (d, J 3.6 Hz); dP (202 MHz, CDCl3)
35.35; GC tR¼28.55 min; GCeMS (EI, 70 eV) m/z¼359 (9, Mþ), 358
(44), 357 (100), 342 (5), 341 (15), 328 (17), 327 (71), 250 (9), 249
(46), 233 (7), 220 (5), 218 (6), 217 (21), 215 (5), 203 (7), 202 (22), 201
(5), 200 (5), 199 (17), 189 (6), 173 (10), 152 (11), 142 (6), 141 (21), 128
(6), 127 (12), 126 (7), 115 (6), 101 (8), 91 (13), 77 (18), 51 (9%).
Minor Diastereomer: Rf (CH3Cl) 0.15; dH (500 MHz, CDCl3) 0.80
(9H, s), 2.43 (1H, dd, J 6.0, 21.1 Hz), 4.02 (3H, s), 4.44 (1H, d, J
12.9 Hz), 5.87 (1H, dd, J 6.3, 9.8 Hz), 6.56e6.58 (1H, m), 6.59 (1H, d, J
9.5 Hz), 6.70e6.75 (1H, m), 6.89e8.10 (11H, m); dC (126 MHz, CDCl3)
27.1, 36.8 (d, J 17.3 Hz), 38.1 (d, J 63.6 Hz), 42.5 (d, J 2.7 Hz), 55.0,
110.1 (d, J 7.3 Hz), 121.3 (d, J 10.9 Hz), 126.1 (d, J 3.6 Hz), 126.4 (d, J
3.6 Hz), 126.9 (d, J 3.6 Hz), 127.9 (d, J 11.8 Hz), 127.8 (d, J 1.8 Hz),
128.5 (d, J 1.8 Hz), 131.3 (d, J 2.7 Hz), 132.1 (d, J 10.0 Hz), 133.4 (d, J
1.8 Hz), 135.3 (d, J 4.5 Hz), 158.7 (d, J 4.5 Hz); dP (202 MHz, CDCl3)
34.35; GC tR¼28.55 min; GCeMS (EI, 70 eV) m/z¼359 (9, Mþ), 358
(44), 357 (100), 342 (5), 341 (15), 328 (17), 327 (71), 250 (9), 249
(46), 233 (7), 220 (5), 218 (6), 217 (21), 215 (5), 203 (7), 202 (22), 201
(5), 200 (5), 199 (17), 189 (6), 173 (10), 152 (11), 142 (6), 141 (21), 128
(6), 127 (12), 126 (7), 115 (6), 101 (8), 91 (13), 77 (18), 51 (9%).
4.1.36. 1-t-Butyl-5-methoxydibenzophospholane oxide (16d). This
compound was prepared according to general procedure (Method
A) from m-anisylphenyl-p-tolylphosphine oxide (14e) (0.161 g,
0.499 mmol) and tert-butyllithium (0.588 mL, 0.999 mmol, 1.7 M
solution in pentane): yield 0.007 g (5%); pale yellow sticky solid.
Isolated as a mixture of 15e, 15f, 15g and 16e. The same compound
was prepared from t-butylphenylphosphine oxide 18 through
palladium-catalyzed coupling with 3-bromoanizole followed by
reaction with t-BuLi. Yellow pasty solid; Rf (CH3Cl) 0.06; dH
(500 MHz, CDCl3) 1.16 (9H, d, J 15.5 Hz), 4.00 (3H, s), 7.11 (1H, d, J
8.5 Hz), 7.33e7.40 (2H, m), 7.42e7.45 (1H, m), 7.52e7.56 (1H, m),
7.79e7.83 (1H, m), 8.36e8.39 (1H, m); dC (126 MHz, CDCl3) 23.9,
32.8 (d, J 70.8 Hz), 55.4, 115.5 (d, J 2.7 Hz), 122.0 (d, J 8.2 Hz), 126.4
(d, J 9.1 Hz), 127.6 (d, J 10.0 Hz), 128.2 (d, J 10.9 Hz), 129.7 (d, J
8.2 Hz), 129.8 (d, J 11.8 Hz), 129.9 (d, J 96.3 Hz), 132.5 (d, J 92.6 Hz),
132.9 (d, J 1.8 Hz), 141.6 (d, J 19.1 Hz), 156.8 (d, J 11.8 Hz); dP
(202 MHz, CDCl3) 53.75; GC tR¼12.28 min; GCeMS (EI, 70 eV) m/
z¼286 (11, Mþ), 231 (15), 230 (100), 229 (13), 215 (14), 214 (6), 199
(6), 186 (9), 168 (9), 157 (13), 139 (8), 133 (10), 57 (9%).
4.1.39. m-Anisylphenyl(2-tert-butyl-1,2-dihydronaphth-1-yl)phos-
phine oxide (15i). This compound was prepared according to general
procedure (Method A) from m-anisyl-1-naphthylphenylphosphine
oxide (14g) (0.179 g, 0.499 mmol) and tert-butyllithium (0.588 mL,
0.999 mmol, 1.7 M solution in pentane): yield of two diastereomers
(dr¼50:50) 0.119 g (57%). Isolated as a mixture of diastereomers. Rf
(CH3Cl) 0.21; dH (500 MHz, CDCl3) 0.85 (9H, s) and 0.85 (9H, s), 2.87
(1H, t, J 6.31 Hz) and 2.91 (1H, t, J 6.3 Hz), 3.66 (3H, s) and 3.82 (3H, s),
3.93 (1H, d, J 3.2 Hz) and 3.97 (1H, d, J 3.8 Hz), 5.71 (1H, t, J 6.0 Hz)
and 5.73 (1H, t, J 6.0 Hz), 6.19 (1H, d, J 11.0 Hz) and 6.21 (1H, d, J
10.7 Hz), 6.38e6.42 (1H, m) and 6.41e6.44 (1H, m), 6.80e7.86 (13H,
m) and 6.80e7.86 (13H, m); dC (126 MHz, CDCl3) 26.96 and 26.98,
36.7 (d, J 16.4 Hz), 41.7 (d, J 2.7 Hz) and 41.8 (d, J 1.8 Hz), 42.4 (d, J
62.7 Hz) and 42.5 (d, J 62.7 Hz), 55.3 and 55.4, 116.6 (d, J 9.1 Hz) and
117.1 (d, J 10.0 Hz), 117.7 (d, J 1.8 Hz) and 118.3 (d, J 2.7 Hz), 124.0 (d, J
4.1.37. 1-t-Butyl-5-methoxy-7-methyldibenzophospholane
oxide
(16e). This compound was prepared according to general pro-
cedure (Method A) from m-anisylphenyl-p-tolylphosphine oxide
(14e) (0.161 g, 0.499 mmol) and tert-butyllithium (0.588 mL,
0.999 mmol, 1.7 M solution in pentane): yield 0.003 g (2%). Isolated