Hetero-Diels–Alder Reaction of Phosphorylated Nitroso Alkenes

Supporting Information
Hetero-Diels–Alder Reaction of Phosphorylated
Nitroso Alkenes with Enol Ethers on Water: a Clean
Approach Towards 1,2-Oxazine Derivatives
Jesús M. de los Santos, Roberto Ignacio, Zouhair Es Sbai, Domitila Aparicio, Francisco
Palacios*
Departamento de Química Orgánica I, Facultad de Farmacia, Centro de Investigaciones y
Estudios Avanzados “Lucio Lascaray”, Universidad del País Vasco, Paseo de la Universidad, 7.
01006 Vitoria, Spain.
e-mail: [email protected]
Table of Contents
1. NMR spectra of functionalized α-halooximes and starting materials……………….…..…..S2
2. NMR spectra of substituted 1,2-oxazines...……………………………..……...……..……..S6
S1
1. NMR spectra of functionalized α-halooximes and starting materials
S2
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
f1 (ppm)
S3
5.0
1 1 .7 1
7 .1 0
2 .0 5
0 .5 3
2 9 .3 7
2 .0 0
1 .0 0
12.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
-1.0
12.5
12.0
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
f1 (ppm)
S4
5.0
4.5
4.0
4 .34
1 .99
2 .13
9 .91
1 .00
13.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
0.0
-0.5
-1.0
S5
2. NMR spectra of substituted 1,2-oxazines
S6
S7
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
f1 (ppm)
S8
4.5
3.5
3.0
2.5
2.0
1 1 .1 5
1 .1 2
1 .5 8
1 .4 7
4.0
7 .4 8
10.5
1 .5 3
11.0
3 .2 9
1 .0 0
11.5
1.5
1.0
0.5
0.0
-0.5
-1.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
f1 (ppm)
S9
4.5
4.0
3.5
3.0
2.5
2.0
1.5
2 1 .1 9
4 .3 9
1 9 .0 8
3 .4 2
3 .3 8
2 1 .7 7
1 .0 0
11.0
1.0
0.5
0.0
-0.5
-1.0
S10
S11
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
f1 (ppm)
S12
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1 0 .1 7
3 .3 3
2 .1 8
1 .5 1
1 0 .6 4
1 .0 0
4 .6 6
1 .9 8
12.0
1.5
1.0
0.5
0.0
-0.5
-1.0
S13
11.5
11.0
10.5
10.0
9.5
9.0
8.5
8.0
7.5
7.0
6.5
6.0
5.5
f1 (ppm)
S14
5.0
4.5
4.0
3.5
3.0
2.5
2.0
5 .87
1 .01
0 .96
2 .80
1 .00
1 .03
1 .21
0 .90
8 .22
1 .86
12.0
1.5
1.0
0.5
0.0
-0.5
-1.0
S15
S16
S17