(
C
25), 91 (100), 77 (6), 71 (12), 65 (9), 59 (9). Anal. Calcd for
(383.44): C 68.91, H 6.57, N 3.65. Found: C 69.10,
anti-2-(Formylamino)-1-vinyl-2-(4-methoxyphenyl)ethyl mE-
1
22
H25NO
5
thyl Carbonate (anti-6i). H NMR (300 MHz, CDCl ): δ 3.81
3
H 6.55, N 3.64
(broad s, 6H), 5.28-5.47 (m, 4H), 5.63 (ddd, J ) 5.6/10.5/17.3
Hz, 1H), 6.1 (d, J ) 8.5 Hz, 1H), 6.89 (d, J ) 8.8 Hz, 2H), 7.25
anti-2-(Benzyloxycarbonylamino)-1-vinyl-(E)-5-undecyl Meth-
1
13
yl Carbonate (anti-6e). H NMR (200 MHz, CDCl
3
): δ 0.89 (t,
(d, J ) 8.8 Hz, 2H). C NMR (75 MHz, CDCl ): δ 53.4, 54.8,
3
J ) 5.9 Hz, 3H), 1.18-1.40 (m, 6H), 1.40-1.76 (m, 2H), 1.87-
.17 (m, 4H), 3.79 (s, 3H), 3.83-4.04 (m, 1H), 4.72 (d, J ) 9.8
Hz, 1H), 5.11 (s, 2H), 5.11-5.23 (m, 1H), 5.25-5.52 (m, 4H),
5
5.1, 79.6, 113.9, 119.7, 128.0, 128.5, 131.5, 154.8, 159.1, 160.6.
2
GC-MS (70 eV): m/z (%) 247 (8), 164 (100), 147 (15), 137 (22),
36 (25), 121 (18), 115 (11), 109 (21), 91 (16), 77 (21), 65 (8), 51
8). Anal. Calcd for C14 (279.29): C 60.21, H 6.14, N 5.02.
1
(
5
(
5
1
1
.82 (ddd, J ) 6.2/10.6/17.0 Hz, 1H), 7.29-7.48 (m, 5H). 13C NMR
75 MHz, CDCl ): δ 14.1, 22.5, 28.9, 29.2, 29.7, 31.4, 32.5, 53.0,
H17NO
5
3
Found: C 60.18, H 6.16, N 5.01
4.9, 66.9, 80.3, 119.1, 127.7, 128.1, 128.4, 128.5, 131.8, 132.1,
36.3, 155.0, 156.0. GC-MS (70 eV): m/z (%) 220 (7), 180 (39),
62 (7), 152 (14), 124 (20), 115 (9), 108 (8), 95 (31), 81(23), 69
100), 55 (61). Anal. Calcd for C23H33NO (403.51): C 68.46, H
5
.24, N 3.47. Found: C 68.71, H 8.26, N 3.46
anti-2-(ethoxycarbonylamino)-1-vinyl-2-phenylethyl methyl
1
carbonate (anti-6j). H NMR (300 MHz, CDCl
3
): δ 1.23 (t, J )
7
1
7
.0 Hz, 3H), 3.80 (s, 3H), 4.11 (q, J ) 7.0 Hz, 2H), 4.99-5.10 (m,
H), 5.24-5.46 (m, 4H), 5.60 (ddd, J ) 5.8/10.7/16.6 Hz, 1H),
.24-7.39 (m, 5H). 13C NMR (50 MHz, CDCl
): δ 14.4, 54.9,
(
8
anti-2-(Benzyloxycarbonylamino)-1-vinyl-7-chloroepthyl Meth-
3
1
57.2, 61.1, 79.8, 119.6, 127.2, 127.4, 127.8, 128.5, 131.3, 137.6,
154.9, 155.8. GC-MS (70 eV): m/z (%) 178 (100), 134 (12), 132
(17), 115 (6), 106 (49), 104 (18), 91 (7), 79 (27), 77 (17), 59 (9).
yl Carbonate (anti-6f). H NMR (200 MHz, CDCl
.54 (m, 6H), 1.64-1.84 (m, 2H), 3.51 (t, J ) 6.5 Hz, 2H), 3.79
s, 3H), 3.84-4.02 (m, 1H), 4.74 (d, J ) 9.2 Hz, 1H), 5.11 (s,
H), 5.11-5.22 (m, 1H), 5.32 (dt, J ) 1.4/10.4 Hz, 1H), 5.37 (dt,
J ) 1.4/16.9 Hz, 1H), 5.80 (ddd, J ) 6.1/10.4/16.9 Hz, 1H), 7.34-
3
): δ 1.23-
1
(
2
Anal. Calcd for C15
Found: C 61.37, H 6.52, N 4.79
-[tert-Butoxycarbonylamino-(2,2-dimethyl-1,3-dioxolan-4-yl)-
5
H19NO (293.32): C 61.42, H 6.53, N 4.78.
7
3
1
1
7
.39 (m, 5H). 13C NMR (75 MHz, CDCl
3
): δ 25.6, 26.9, 30.0,
1
2.7, 45.2, 53.6, 55.2, 67.2, 80.5, 119.5, 128.4, 128.5, 128.8, 132.4,
36.6, 155.3, 156.4. GC-MS (70 eV): m/z (%) 200 (1), 172 (4),
60 (7), 141 (4), 126 (20), 124 (25), 116 (48), 115 (100), 81 (48),
methyl]-allyl Methyl Carbonate (6k). The title product was
obtained in 82% yield as a 85:15 mixture of syn and anti isomers
after flash chromatography on silica. The crude reaction mixture
was directly cyclized to oxazolidinones 8k, which can be easily
separated by flash chromatography on silica. See Supporting
1 (70), 69 (27), 59 (26), 55 (23). Anal. Calcd for C19H26ClNO
5
(
3
383.87): C 59.45, H 6.83, N 3.65. Found: C 59.55, H 6.81, N
.64
anti-2-(Benzyloxycarbonylamino)-1-vinyl-4-benzenesulfonyl-
1
13
Information for copies of H and C NMR spectra.
1
butyl Methyl Carbonate (anti-6g). Mp: 102-104 °C. H NMR
300 MHz, CDCl ): δ 1.79-1.98 (m, 1H), 2.03-2.21 (m, 1H),
.11-3.22 (m, 2H), 3.79 (s, 3H), 3.88-4.02 (m, 1H), 4.91 (d, J )
2-(tert-Butoxycarbonylamino-3-phenyl-propionylamino)-1-
vinyl-4-phenylbutyl Methyl Carbonate (6l). The title product was
obtained in 92% yield as a 60:40 mixture of syn and anti isomers
after flash chromatography on silica. See Supporting Information
(
3
3
9
1
1
7
.6 Hz, 1H), 5.08 (s, 2H), 5.10-5.18 m, 1H), 5.34 (dt, J ) 1.2/
0.6 Hz, 1H), 5.37 (dt, J ) 1.2/17.3 Hz, 1H), 5.75 (ddd, J ) 6.0/
0.6/17.3 Hz, 1H), 7.26-7.44 (m, 4H), 7.58 (t, J ) 7.4 Hz, 2H),
.68 (t, J ) 7.4 Hz, 1H), 7.89 (d, J ) 7.4 Hz, 2H). 13C NMR (75
3
): δ 22.8, 52.2, 53.0, 54.9, 66.9, 79.5, 119.7, 127.8,
27.9, 128.0, 128.4, 129.2, 131.5, 133.7, 136.0, 138.8, 154.7, 156.0.
1
13
for copies of H and C NMR spectra.
Acknowledgment. This work was supported by MIUR
Rome) PRIN project grant “Sintesi e Stereocontrollo di
Molecole Organiche per lo Sviluppo di Metodologie Innovative
di Interesse Applicativo”.
MHz, CDCl
1
(
GC-MS (70 eV): m/z (%) 281 (2), 207 (5), 197 (9), 153 (6), 143
(
(
5
13), 142 (11), 126 (15), 125 (18), 112 (41), 95 (100), 77 (81), 68
62), 57 (21), 51 (35). Anal. Calcd for C22 S (447.50): C
9.05, H 5.63, N 3.13. Found: C 58.88, H 5.65, N 3.13
-(Benzyloxycarbonylamino)-1-vinyl-2-ethoxycarbonylethyl
H25NO
7
Supporting Information Available: Experimental procedures
2
1
13
for stereochemical assignment and copies of H and C NMR
spectra of new compounds. This material is available free of charge
via the Internet at http://pubs.acs.org.
Methyl Carbonate (6h). The title product was obtained in 98%
yield as a 65:35 mixture of syn and anti isomers after flash
chromatography on silica. See Supporting Information for copies
1
13
of H and C NMR spectra.
JO062265N
J. Org. Chem, Vol. 72, No. 5, 2007 1837