NMR-Data for

Asymmetric Synthesis of Indolines through Intramolecular Shifting of Aromatic Sulfinyl Groups. Role of the ,-Stacking Interactions in these Novel SNAr Processes. Jos L. Garca Ruano,* Alejandro Parra, Vanesa Marcos, Carlos del Pozo, Silvia Cataln, Silvia Monteagudo, Santos Fustero*

OMe

HN Ph TolOS

anti-3a

OMe

HN Ph TolOS

anti-3a

OMe

HN Ph TolOS

syn-4a

OMe

HN Ph TolOS

syn-4a

OMe

HN Ph TolOS

anti-3e

OMe

HN Ph TolOS

anti-3e

Ph HN TolOS OMe

anti-3f

Ph HN TolOS OMe

anti-3f

Ph HN TolOS OMe

syn-4f

Ph HN TolOS OMe

syn-4f

Ph HN TolOS

anti-3g

Ph HN TolOS

anti-3g

Ph HN TolOS Cl

anti-3h

9.5

8.5

7.5

6.5

5.5

4.5 (ppm)

3.5

2.5

1.5

0.5

-0.5

-1.5

Ph HN TolOS Cl

anti-3h

200

180

160

140

120

100 (ppm)

80

60

40

20

Cl HN Ph TolOS

anti-3i

Cl HN Ph TolOS

anti-3i

OMe HN TolOS Cl

anti-3j

9.5

8.5

7.5

6.5

5.5

4.5 (ppm)

3.5

2.5

1.5

0.5

-0.5

OMe HN TolOS Cl

anti-3j

200

180

160

140

120

100 (ppm)

80

60

40

20

Cl

HN Ph TolOS

anti-3k

Cl

HN Ph TolOS

anti-3k

Cl

HN TolOS Cl

anti-3l

Cl

HN TolOS Cl

anti-3l

CN

HN TolOS OMe

anti-3m

CN

HN TolOS OMe

anti-3m

200

180

160

140

120

100 (ppm)

80

60

40

20

CN

HN TolOS

anti-3n

CN

HN TolOS

anti-3n

200

180

160

140

120

100 (ppm)

80

60

40

20

CN

HN TolOS

anti-3p

CN

HN TolOS

anti-3p

200

180

160

140

120

100 (ppm)

80

60

40

20

OMe MeO HN Ph TolOS

OMe

syn-4o

OMe MeO HN TolOS

OMe

syn-4p

OMe

OMe MeO HN TolOS

OMe

syn-4p

OMe

PMP N

Me

trans-5a

10.0

9.0

8.0

7.0

6.0

5.0 (ppm)

4.0

3.0

2.0

1.0

0.0

PMP N

Me

trans-5a

200

190

180

170

160

150

140

130

120

110

100 (ppm)

90

80

70

60

50

40

30

20

10

PMP N OMe

Me

trans-5b

PMP N OMe

Me

trans-5b

200

180

160

140

120 (ppm)

100

80

60

40

20

PMP N

Me

Me

trans-5c

PMP N

Me

Me

trans-5c

200

180

160

140

120

100 (ppm)

80

60

40

20

PMP N

Cl

Me

trans-5d

9.5

8.5

7.5

6.5

5.5

4.5 (ppm)

3.5

2.5

1.5

0.5

-0.5

PMP N

Cl

Me

trans-5d

200

180

160

140

120

100 (ppm)

80

60

40

20

PMP N CN

Me

trans-5e

PMP N CN

Me

trans-5e

200

180

160

140

120

100 (ppm)

80

60

40

20

Ph N OMe

Me

trans-5f

9.5

8.5

7.5

6.5

5.5

4.5 (ppm)

3.5

2.5

1.5

0.5

-0.5

Ph N OMe

Me

trans-5f

200

180

160

140

120

100 (ppm)

80

60

40

20

Ph N

Me

trans-5g

Ph N

Me

trans-5g

200

180

160

140

120

100 (ppm)

80

60

40

20

Cl

Me

trans-5h

Cl

Me

trans-5h

Cl

OMe

Me

trans-5j

Cl

OMe

Me

trans-5j

200

180

160

140

120

100 (ppm)

80

60

40

20

Cl

Me

trans-5k

Cl

Me

trans-5k

200

180

160

140

120 (ppm)

100

80

60

40

20

Cl

Cl

Me

trans-5l

Cl

Cl

Me

trans-5l

CN

OMe

Me

trans-5m

CN

OMe

Me

trans-5m

200

180

160

140

120 (ppm)

100

80

60

40

20

OMe OMe N CN

Me

trans-5p

OMe OMe N CN

Me

trans-5p

200

180

160

140

120

100 (ppm)

80

60

40

20

NH2 CF3 TolOS

anti-11

NH2 CF3 TolOS

anti-11

NH2 CF3 TolOS

anti-11

-20

-40

-60

-80

-100 (ppm)

-120

-140

-160

-180

-200

OMe MeO HN TolOS PMP

16

OMe MeO HN TolOS PMP

16

200

180

160

140

120

100 (ppm)

80

60

40

20