1
90 J . Org. Chem., Vol. 65, No. 1, 2000
Adam et al.
1
[
1-(p-Br om o)p h en yl]-1-p r op yl Ben zoa te (2c). H NMR
400 MHz, CDCl ): δ 8.08 (d, J ) 6.96 Hz, 2H), 7.58 (t, J )
.32 Hz, 1H), 7.47 (q, 4H), 7.29 (t, J ) 8.44 Hz, 2H), 5.86 (t, J
3-Meth yl-1-p h en ylbu ta n -1-ol (1g). MDGC: DB-Wax, 80
to 240 °C (5 °C/min); ethyl, 80 °C (24 min isothermal) to 200
°C (1 °C/min).
(
7
)
(
3
6.64 Hz, 1H), 1.96 (m, 2H), 0.95 (t, J ) 7.36 Hz, 3H). CD
acetonitrile): 232 nm, ∆ꢀ ) -10.9 (R enantiomer); 233 nm,
1
3
-Meth yl-1-p h en yl-1-bu tyl Ben zoa te (2g). H NMR (400
MHz, CDCl ): δ 8.09 (d, J ) 7.0 Hz, 2H), 7.56 (t, J ) 7.32 Hz,
H), 7.45 (t, J ) 7.72 Hz, 4H), 7.35 (t, J ) 6.96 Hz, 2H), 7.30
d, J ) 6.96 Hz, 1H), 6.07 (m, 1H), 1.75 (m, 2H), 1.12 (m, 1H),
.00 (d, J ) 6.24 Hz, 3H), 0.98 (d, J ) 6.24 Hz, 3H). CD
acetonitrile): 224 nm, ∆ꢀ ) -6.2 (R enantiomer).
1-P h en yl)h exa n -1-ol (1h ). MDGC: DB-Wax, 80 to 240
C (10 °C/min); â, 80 °C (18 min isothermal) to 200 °C (2 °C/
3
∆
ꢀ ) +10.0 (S enantiomer).
1-(p-Br om o)p h en yl]-1-p r op yl Aceta te (3c). GC-MS:
m/z (%) 256 (0.01), 229 (55), 227 (57), 216 (29), 214 (31), 199
11), 198 (32), 197 (12), 196 (33), 187 (94), 186 (14), 185 (100),
71 (33), 169 (35), 157 (23), 118 (31), 117 (91), 116 (20), 115
51), 90 (12), 89 (13), 78 (16), 77 (45), 76 (18), 75 (18), 51 (19),
1
(
1
(
[
(
1
(
(
°
4
3 (83).
(
min).
1-P h en yl)-1-h exyl Ben zoa te (2h ). H NMR (400 MHz,
CDCl ): δ 8.09 (d, J ) 8.12, 2H), 7.52 (t, J ) 6.6 Hz, 1H), 7.38
(m, 7H), 5.98 (t, J ) 6.96 Hz, 1H), 2.04 (m, 1H), 1.87 (m, 1H),
.43 (m, 2H), 1.25 (m, 4H), 0.87 (t, J ) 7.0 Hz, 3H). CD
acetonitrile): 225 nm, ∆ꢀ ) -4.9 (R enantiomer); 224 nm; ∆ꢀ
+9.6 (S enantiomer).
1-P h en yl)-1-h exyl Aceta te (3h ). GC-MS: m/z (%) 220 (4),
78 (35), 149 (28), 117 (28), 107 (100), 105 (13), 104 (37), 91
1-P h en yl)-2-p r op en -1-ol (1d ). MDGC: DB-Wax, 80 to
40 °C (5 °C/min); â, 80 °C (27 min isothermal) to 200 °C (1
1
(
2
°
3
C/min).
(
1-P h en yl)-2-p r op en yl Ben zoa te (2d ). 1H NMR (400
MHz, CDCl ): δ 8.11 (d, J ) 5.88 Hz, 2H), 7.58 (t, J ) 7.68
Hz, 1H), 7.46 (t, J ) 6.6 Hz, 4H), 7.39 (t, J ) 7 Hz, 2H), 7.33
d, J ) 7.36 Hz, 1H), 6.52 (m, 1H), 6.14 (m, 1H), 5.41 (d, J )
.9 Hz, 1H), 5.31 (d, J ) 10.28 Hz, 1H). CD (acetonitrile): 224
nm, ∆ꢀ ) -3.6 (R enantiomer); 223 nm, ∆ꢀ ) +3.6 (S
1
(
)
3
(
(
8
1
(30), 79 (16), 77 (14), 43 (59), 41 (6).
enantiomer).
(
1-P h en yl)-2-p r op en yl Aceta te (3d ). GC-MS: m/z (%)
76 (1), 134 (71), 133 (21), 117 (28), 116 (63), 115 (100), 105
27), 91 (16), 77 (20), 51 (12), 43 (51).
,2 Dim eth yl-1-p h en ylp r op a n -1-ol (1e). MDGC; DB-
(1-P h en yl)h ep ta n -1-ol (1i). MDGC: DB-Wax, 100 to 240
°C (5 °C/min); ethyl, 100 °C (28 min isothermal) to 200 °C (2
1
(
°C/min).
2
1
(
1-P h en yl)-1-h ep tyl Ben zoa te (2i). H NMR (400 MHz,
Wax: 60 to 240 °C (4 °C/min); ethyl: 60 °C (34 min isothermal)
to 200 °C (2 °C/min).
2
CDCl
3
): δ 8.09 (d, J ) 8.09 Hz, 2H), 7.56 (t, J ) 7.36 Hz, 1H),
.44 (q, 4H), 7.35 (t, J ) 7.35 Hz, 2H), 7.29 (d, J ) 6.99 Hz,
H), 5.97 (t, J ) 6.98 Hz, 1H), 2.05 (m, 1H), 1.9 (m, 1H), 1.25
7
1
(
1
,2 Dim eth yl-1-p h en yl-1-p r op yl Ben zoa te (2e). H NMR
(
3
400 MHz, CDCl ): δ 8.15 (d, J ) 6.64 Hz, 2H), 7.60 (t, J )
m, 8H), 0.86 (t, J ) 6.62 Hz, 3H). CD (acetonitrile): 227 nm,
ꢀ ) -3.7 (R enantiomer); 225 nm, ∆ꢀ ) +6.5 (S enantiomer).
7
2
2
.32 Hz, 1H), 7.50 (t, J ) 7.72 Hz, 2H), 7.39 (d, J ) 6.96 Hz,
∆
H), 7.31 (m, 3H), 5.75 (s, 1H), 1.07 (s, 9H). CD (acetonitrile):
(
1-P h en yl)-1-h ep tyl Aceta te (3i). GC-MS: m/z (%) 234
29 nm, ∆ꢀ ) -2.1 (R enantiomer); 228 nm, ∆ꢀ ) +10.3 (S
enantiomer).
(
C (5 °C/min); â, 80 °C (24 min isothermal) to 200 °C (2 °C/
min).
(
(
3), 192 (34), 149 (31), 117 (26), 107 (100), 104 (46), 91 (33), 79
17), 77 (15), 43 (57).
1-P h en yl)p en ta n -1-ol (1f). MDGC: DB-Wax, 100 to 240
(
1-P h en yl)-1-d ecyl Ben zoa te (2j). 1H NMR (400 MHz,
CDCl ): δ 7.9 (dd, J ) 7.33 Hz, 2H), 7.37 (t, J ) 7.33 Hz, 1H),
7.15 (m; 7H), 5.8 (t, J ) 6.86 Hz, 1H), 1.74 (m, 2H), 1.09 (m,
°
3
1
(
1-P h en yl)-1-p en tyl Ben zoa te (2f). H NMR (250 MHz,
CDCl ): δ 8.10 (d, J ) 6.7 Hz, 2H), 7.57 (t, J ) 7.33 Hz, 1H),
.38 (m, 7H), 5.99 (t, J ) 6.1 Hz, 1H), 2.00 (m, 2H), 1.37 (m,
H), 0.90 (t, J ) 6.73 Hz, 3H). CD (acetonitrile): 223 nm, ∆ꢀ
+3.5 (S enantiomer).
1-P h en yl)-1-p en tyl Aceta te (3f). GC-MS: m/z (%) 206
18), 165 (19), 164 (93), 150 (11), 149 (87), 146 (25), 131 (11),
18 (26), 117 (92), 115 (37), 108 (37), 107 (100), 105 (56), 104
82), 103 (21), 92 (14), 91 (88), 79 (76), 78 (31), 77 (76), 65 (16),
1 (25), 43 (84), 41 (26).
1
)
4H), 0.68 (t, J ) 6.4 Hz, 3H). CD (acetonitrile): 226 nm, ∆ꢀ
+9.3 (S enantiomer).
3
7
4
)
Ack n ow led gm en t. We thank the Deutsche Fors-
(
chungsgemeinschaft (SFB 347 “Selektive Reaktionen
Metall-aktivierter Molek u¨ le”) and the Fonds der Che-
mischen Industrie for their generous financial support.
(
1
(
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J O991424I