This journal is © The Royal Society of Chemistry 2012 ... fileendo -1b 174.42 174.25 168.73 168.55 166.24 135.17 128.75 128.55 128.10 75.67 63.14 63.03 62.17 61.66 51.77 49.33 43.12

endo-1a

9.57

3.19

1.00

1.05

1.00

7.52

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2012

endo-1b

13.99

14.06

14.12

43.12

49.33

51.77

61.66

62.17

63.03

63.14

75.67

128.10

128.55

128.75

135.17

166.24

168.55

168.73

174.25

174.42


endo-1c

9.31

0.83

0.99

1.00

7.32

1.91

3.05

14.00

14.06

14.13

49.61

52.11

62.15

62.32

63.14

63.17

76.19

126.67

129.10

129.36

131.46

166.42

168.72

168.97

173.77

174.00


endo-1d

8.35

0.99

5.87

7.16

13.95

14.00

14.18

50.47

52.62

52.75

53.40

61.63

61.81

61.90

62.70

62.73

74.61

168.70

168.92

170.27

170.97

171.23

NH

CO2Et

CO2Et

EtO2C

MeO2C CO2Me


endo-1e

3.02

8.33

2.03

1.07

4.97

1.00

1.00

9.41

2.50

NH

CO2Et

CO2Et

EtO2C

PhO2S SO2Ph


endo-1f, exo-1f and endo-1f´

18.52

0.89

3.46

0.73

1.17

2.77

2.16

0.75

0.88

1.00

13.90

0.89

3.46

0.73

1.17

2.77

2.16

0.75

0.88

1.00

14.02

14.06

14.11

14.16

14.26

33.52

34.60

36.00

46.64

46.80

49.46

52.20

52.29

52.51

61.53

61.57

62.33

62.50

62.56

71.61

75.31

168.91

169.66

170.28

170.91

171.29

171.51

171.87

172.43


1g

13.90

13.98

14.18

14.33

14.49

59.81

60.25

60.31

62.10

62.49

77.24

92.91

146.98

147.12

163.46

166.76

166.91

166.97

169.32


1h and 1i

7.38

14.43

4.97

4.16

3.38

9.33

0.91

0.98

1.00

0.38

1.17

13.91

14.11

61.48

62.29

62.49

62.65

62.81

62.91

66.01

66.09

79.22

82.88

137.86

150.88

150.95

162.60

162.70

168.04

168.17

168.50

168.56

170.31

170.54


endo-cis-2a and endo-trans-2a

10.66

3.39

1.69

2.09

0.63

2.00

0.80

7.93

14.14

14.25

25.37

25.54

47.60

48.77

49.91

61.83

61.87

62.02

62.17

62.42

63.00

168.98

169.73

171.71

174.96

175.39

176.62


endo-cis-2b

6.48

2.10

2.00

4.26

2.03

5.00

1.24

1.26

1.26

1.28

1.31

3.53

3.54

3.55

3.56

3.93

4.21

4.23

4.25

4.28

4.58

7.26

7.27

7.29

7.29

7.30

7.30

7.30

14.08

42.99

49.77

62.04

63.00

128.06

128.57

128.70

135.24

168.80

174.63


endo-cis-2c

6.20

0.93

2.00

2.04

4.10

1.94

3.15


endo-trans-2c

6.55

0.85

0.97

0.96

5.24

1.00

2.58

3.36

14.07

14.18

47.70

49.24

61.95

62.16

62.36

62.91

126.42

128.90

129.21

131.51

169.91

171.50

174.59

175.66


endo-cis-3a

3.40

2.75

2.92

1.00

0.97

2.80

1.00

2.50

14.17

24.62

25.39

50.43

53.13

57.07

61.98

62.11

69.38

169.45

171.65

174.99

175.19


endo-cis-3f

4.76

2.75

1.19

0.98

1.00

3.35

3.13

3.83

14.26

25.92

40.69

47.42

52.41

52.67

61.59

62.95

66.34

172.75

173.46

176.32


endo-trans-3f and endo-cis-3f´

14.63

14.74

21.72

25.97

28.82

32.77

33.42

39.54

47.56

50.91

52.52

52.92

53.10

53.41

53.77

58.48

59.64

61.84

63.23

65.86

68.75

172.07

172.67

174.09

174.71

176.89


endo-cis-3d

4.99

2.80

0.98

2.84

2.95

3.51

1.00

3.37

14.22

24.89

49.62

52.37

52.57

52.71

56.85

61.67

61.79

68.42

170.64

172.28

172.97

173.83


endo-cis-3e

0.12

1.15

13.99

23.74

52.73

61.49

62.18

69.42

69.49

72.97

128.35

128.93

129.25

129.44

134.21

134.44

138.14

140.39

170.14

171.23


endo-cis-4a

14.07

14.12

25.35

42.15

50.39

56.63

61.73

62.12

62.31

73.59

127.23

128.26

130.44

135.73

169.62

170.13

174.96

175.06


endo-cis-4b

6.40

0.97

2.80

1.00

5.00

1.97

10.20

0.00

1.21

1.23

1.26

1.28

1.31

2.87

2.91

3.29

3.33

3.37

3.39

3.52

3.55

4.18

4.20

4.21

4.22

4.56

4.57

7.23

7.24

7.25

7.26

7.27

7.28

7.29

7.29

7.30

7.30

14.02

14.11

42.24

42.99

50.36

56.57

61.92

62.13

62.33

73.73

127.23

128.03

128.27

128.59

128.68

130.48

135.25

135.78

169.38

169.93

174.58

174.68


endo-cis-4c

6.13

1.00

1.00

2.00

1.05

5.06

10.59

1.259

1.284

1.308

1.332

2.937

2.984

3.334

3.548

3.553

3.574

3.650

3.679

4.126

4.155

4.166

4.194

4.212

4.215

4.221

4.236

4.239

4.245

4.260

4.263

4.269

4.293

7.173

7.177

7.182

7.192

7.200

7.205

7.252

7.259

7.268

7.278

7.288

7.297

7.365

7.383

7.388

7.393

7.408

7.413

7.426

7.433

7.456

13.926

13.994

42.344

50.410

56.616

62.179

62.354

74.141

126.573

127.188

128.200

128.942

129.229

130.399

135.619

169.729

170.100

174.021

174.168


endo-cis-4d

8.02

1.00

1.86

1.24

2.87

2.87

2.40

6.24

7.09

14.06

14.20

42.58

49.30

52.41

52.56

54.79

61.61

61.68

61.97

72.26

127.14

128.13

128.25

130.09

130.25

130.63

130.88

135.91

170.52

171.89

172.31

172.91


exo-cis-4e

3.07

3.50

0.91

0.82

5.07

1.05

1.00

1.00

5.47

10.14

2.45

0102030405060708090100110120130140150160170180190200δ (ppm)

0.13

13.84

14.00

40.98

61.07

62.24

62.35

69.38

71.99

73.82

127.40

128.38

128.78

129.12

129.24

129.42

130.72

134.28

134.43

134.70

138.51

139.52

169.62


endo-cis-5a

13.81

13.98

20.83

25.19

49.96

53.11

56.21

60.19

61.22

61.78

74.43

127.08

128.18

128.38

137.76

169.25

169.89

174.80

175.07


endo-trans-5a

14.24

25.18

47.30

50.38

53.69

59.84

61.72

74.06

126.02

128.57

128.92

135.42

169.35

173.52

174.10

175.56


endo-cis-5f

3.70

1.65

0.23

0.21

1.06

0.51

3.23

2.71

1.06

1.00

0.04

0.15

0.45

2.27

3.78

1.92

14.225

14.300

33.820

40.429

47.101

52.117

52.215

52.908

54.046

54.384

58.571

58.717

61.114

61.477

62.495

75.766

126.170

126.909

127.071

128.083

128.436

140.188

172.242

173.141

173.605


endo-trans-5f

1.17

2.87

1.09

2.04

2.91

5.67

2.54

1.00

0.99

0.91

1.97

0.83

5.44

2.31

14.32

32.69

50.63

51.50

53.41

58.46

61.34

126.04

126.31

127.92

128.25

128.30

128.50

137.46

172.55

172.95

173.87


endo-cis-5d

3.00

2.28

1.31

3.17

3.07

1.58

3.02

2.73

1.58

1.35

1.39

2.28

1.15

5.29

0.93

2.28

14.02

14.29

49.74

51.05

51.87

52.35

52.58

52.73

53.25

53.54

54.72

56.25

60.71

60.87

61.44

61.68

74.97

75.65

126.39

127.02

127.34

128.13

128.25

128.49

137.01

140.89

170.84

171.12

171.30

171.43

171.72

172.09

172.84

173.46


exo-cis-5d

6.28

1.81

0.70

3.00

1.52

1.64

2.82

3.17

3.36

1.19

1.26

4.52

0.31

0.66

6.35

1.82

2.55

14.28

49.76

51.84

52.57

52.76

53.10

53.57

54.74

58.17

60.88

61.58

61.71

61.90

75.18

75.65

126.41

126.47

127.04

127.36

128.05

128.24

128.51

137.02

139.66

171.14

171.46

171.57

171.76

171.96

172.10


exo-trans-5e

3.78

1.07

0.89

3.05

0.57

2.31

1.12

1.00

1.11

34.19

0.14

14.00

29.84

49.65

53.23

60.85

62.31

69.38

74.65

75.11

128.21

128.30

128.50

128.56

128.80

128.95

129.04

129.20

129.28

129.33

129.87

134.01

134.25

134.83

136.82

138.59

140.09

170.08


8

1.02

1.29

2.31

1.82

1.63

1.58

1.60

4.32

1.99

1.78

1.32

9.97

18.75

41.12

44.21

44.54

47.22

50.01

56.48

60.29

60.87

61.52

65.15

65.32

69.47

127.34

128.06

128.20

128.39

128.61

128.72

128.83

128.93

129.52

130.56

131.11

132.23

134.91

136.34

137.16


Documents

This journal is © The Royal Society of Chemistry 2012 ... fileendo -1b 174.42 174.25 168.73 168.55 166.24 135.17 128.75 128.55 128.10 75.67 63.14 63.03 62.17 61.66 51.77 49.33 43.12