FULL PAPERS
2H), 7.39 (t, J=15.2 Hz, 2H), 7.34–7.27 (m, 1H), 7.20 (s,
2H), 3.53 (s, 2H), 3.42 (s, 2H), 2.89–2.73 (m, 4H), 2.30 (s,
3H), 2.10–1.97 (m, 2H); 13C NMR (100 MHz, CDCl3) d
206.8, 141.4, 140.8, 139.7, 137.7, 134.0, 128.7, 127.2, 127.1,
127.0, 120.4, 72.1, 39.1, 37.6, 37.1, 19.2, 17.8; IR (neat) 2919,
1695, 1316 cmÀ1; HRMS (TOF) calcd for C21H20O2 304.1463,
found 304.1466.
6-(4-Chlorophenyl)-1,4-dimethyl-2-tosylisoindoline(4d).
Amorphous solid, 49 mg, 60%; H NMR (400 MHz, CDCl3)
1
d 7.77 (d, 2H, J=8 Hz), 7.42–7.35 (m, 4H), 7.28 (d, 2H, J=
8 Hz), 7.18 (s, 1H), 7.05 (s, 1H), 4.95 (d, 1H, J=8 Hz), 4.69
(d, 1H, J=16 Hz, 4 Hz), 4.49 (d, 1H, J=16 Hz), 2.38 (s,
3H), 2.24 (s, 3H), 1.69 (d, 3H, J=8 Hz); 13C NMR
(100 MHz, CDCl3) d 143.6, 142.3, 140.4, 139.2, 134.5, 133.5,
133.4, 133.0, 129.8, 128.9, 128.3, 127.5, 127.5, 118.2, 62.2,
6’-(4-Chlorophenyl)-4’-methyl-1’,3’-dihydrospiro[cyclohex-
ane-1,2’-indene]-2,6-dione (2m). Yellow solid, mp 65–688C,
55 mg, 81%; 1H NMR (400 MHz, CDCl3) d 7.43 (d, J=
8.3 Hz, 2H), 7.34 (d, J=8.5 Hz, 2H), 7.14 (s, 2H), 3.51 (s,
2H), 3.40 (s, 2H), 2.77 (t, J=6.7 Hz, 4H), 2.28 (s, 3H),
2.08–1.98 (m, 2H); 13C NMR (100 MHz, CDCl3) d 206.69,
139.95, 139.84, 139.47, 138.04, 134.13, 132.97, 128.74, 128.31,
126.93, 120.16, 71.96, 38.97, 37.54, 37.13, 19.15, 17.73; IR
(neat) 2925, 1698, 1336 cmÀ1; HRMS (TOF) Calcd for
C21H19ClO2 338.1074, Found, 338.1079.
53.0, 24.0, 21.5, 18.7; IR (neat) 3476, 1619, 1163 cmÀ1
;
HRMS (TOF) Calcd for C23H22ClNO2S 411.1060; Found,
411.1056.
1,4-Dimethyl-6-(thiophen-2-yl)-2-tosylisoindoline(4e).
1
Amorphous solid, 64 mg, 84%; H NMR (400 MHz, CDCl3)
d 7.75 (d, 2H, J=8 Hz), 7.28 (d, 2H, J=8 Hz), 7.24–7.21
(m, 3H), 7.11 (s, 1H), 7.04 (dd, 1H, J=8 Hz, 4 Hz), 4.92
(dd, 1H, J=12 Hz, 8 Hz), 4.66 (dd, 1H, J=16 Hz, 12 Hz),
4.46 (d, 1H, J=16 Hz), 2.37 (s, 3H), 2.21 (s, 3H), 1.68 (d,
3H, J=8 Hz); 13C NMR (100 MHz, CDCl3) d 143.8, 143.6,
142.3, 134.6, 134.5, 133.3, 133.0, 129.8, 128.0, 127.5, 126.5,
124.9, 123.2, 117.2, 62.1, 53.0, 24.0, 21.5, 18.6; IR (neat)
3475, 1620, 1190 cmÀ1; HRMS (TOF) Calcd for C21H21NO2S2
383.1014; Found, 383.1021.
Ethyl
7-methyl-5-phenyl-1H-indene-2-carboxylate(2n).
1
Amorphous solid, 40 mg, 72%; H NMR (400 MHz, CDCl3)
d 7.76 (t, 1H, J=4 Hz), 7.60–7.56 (m, 3H), 7.45–7.42 (m,
2H), 7.38 (s, 1H), 7.36–7.32 (m, 1H), 4.33 (dd, 2H, J=
12 Hz, 8 Hz), 3.62 (d, 2H, J=4 Hz), 2.44 (s, 3H), 1.38 (t,
3H, J=8 Hz); 13C NMR (100 MHz, CDCl3) d 165.1, 143.1,
142.6, 141.3, 140.7, 137.7, 133.8, 128.7, 127.9, 127.3, 127.2,
1-Ethyl-4-methyl-6-phenyl-2-tosylisoindoline(4 f). Amor-
phous solid, 59 mg, 76%; 1H NMR (400 MHz, CDCl3) d
7.75 (d, 2H, J=8 Hz), 7.51–7.48 (m, 2H), 7.42–7.38 (m,
2H), 7.34–7.32 (m, 1H), 7.26 (d, 2H, J=8 Hz), 7.22 (s, 1H),
7.09 (s, 1H), 5.06–5.05 (m, 1H), 4.65 (dd, 1H, J=16 Hz,
4 Hz), 4.56 (d, 1H, J=8 Hz), 2.36 (s, 3H), 2.33–2.24 (m,
1H), 2.24 (s, 3H), 1.97–1.91 (m, 1H), 0.79 (t, 3H, J=8 Hz);
13C NMR (100 MHz, CDCl3) d 143.4, 141.5, 140.8, 140.1,
134.8, 134.2, 132.6, 129.7, 128.8, 127.6, 127.4, 127.4, 127.1,
118.4, 66.9, 53.5, 29.0, 21.5, 18.8, 7.5; IR (neat) 3415, 1620,
1187 cmÀ1; HRMS (TOF) Calcd for C24H25NO2S 391.1606;
Found, 391.1606.
119.7, 60.5, 37.1, 18.8, 14.4; IR (neat) 3464, 1705, 763 cmÀ1
;
HRMS (TOF) Calcd for C19H18O2 278.1307; Found,
278.1308.
1,4-Dimethyl-6-phenyl-2-tosylisoindoline (4a). Amor-
phous solid, 58 mg, 77%; 1H NMR (400 MHz, CDCl3) d
7.78 (d, J=8.0 Hz, 2H), 7.50 ( d, J=6.8 Hz, 2H), 7.41 (t, J=
15.2 Hz, 2H), 7.35 À7.33 (m, 1H), 7.30 (s, 1H), 7.28 (s, 1H),
7.23 (s, 1H), 7.11 (s, 1H), 4.99 À4.95 (m, 1H), 4.73–4.68 (m,
1H), 4.51 (d, J=13.6 Hz, 1H), 2.39 (s, 3H), 2.25 (s, 3H),
1.71 (d, J=6.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) d
143.6, 142.2, 141.8, 140.8, 134.7, 133.1, 132.8, 129.8, 128.8,
127.8, 127.6, 127.4, 127.1, 118.4, 62.3, 53.1, 24.0, 21.5, 18.7;
IR (neat) 3406, 1607, 1179 cmÀ1; HRMS (TOF) calcd for
C23H23NO2S 377.1449, found 377.1448.
1-Ethyl-4-methyl-6-(thiophen-2-yl)-2-tosylisoindoline(4g).
1
Amorphous solid, 64 mg, 80%; H NMR (400 MHz, CDCl3)
d 7.73 (d, 2H, J=8 Hz), 7.26 (s, 1H), 7.24–7.22 (m, 4H),
7.10 (s, 1H), 7.05–7.02 (m, 1H), 5.02–5.01 (m, 1H), 4.61 (dd,
1H, J=16 Hz, 4 Hz), 4.52 (d, 1H, J=12 Hz), 2.36 (s, 3H),
2.30–2.20 (m, 1H), 2.20 (s, 3H), 1.94–1.88 (m, 1H), 0.77 (t,
3H, J=8 Hz); 13C NMR (100 MHz, CDCl3) d 143.9, 143.5,
140.2, 134.8, 134.5, 134.5, 132.8, 129.7, 128.0, 127.3, 126.4,
124.8, 123.1, 117.2, 66.8, 53.5, 29.1, 21.5, 18.6, 7.4; IR (neat)
3415, 1622, 1130 cmÀ1; HRMS (TOF) Calcd for C22H23NO2S2
397.1170; Found, 397.1176.
1,4-Dimethyl-6-(p-tolyl)-2-tosylisoindoline (4b). Amor-
phous solid, 59 mg, 75%; 1H NMR (400 MHz, CDCl3) d
7.78 (d, J=8.3 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.29 (d, J=
8.0 Hz, 2H), 7.22 (d, J=2.0 Hz, 2H), 7.20 (s, 1H), 7.09 (s,
1H), 5.07–4.84 (m, 1H), 4.72–4.68 (m, 1H), 4.50 (d, J=
13.8 Hz, 1H), 2.38 (s, 3H), 2.37 (s, 3H), 2.24 (s, 3H), 1.70
(d, J=6.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) d 143.6,
142.1, 141.7, 137.9, 137.3, 134.6, 132.8, 132.8, 129.8, 129.5,
127.6, 127.6, 126.9, 118.2, 62.3, 53.1, 24.0, 21.5, 21.1, 18.7; IR
(neat) 3408, 1610, 1183 cmÀ1; HRMS (TOF) calcd for
C24H25NO2S 391.1606, found 391.1609.
1,4-Dimethyl-2-(methylsulfonyl)-6-phenylisoindoline(4h).
1
Amorphous solid, 45 mg, 75%; H NMR (400 MHz, CDCl3)
d 7.75–7.73 (m, 2H), 7.45–7.41 (m, 2H), 7.37–7.35 (m, 1H),
7.31 (s, 1H), 7.20 (s, 1H), 5.08 (q, 1H, J=8 Hz), 4.67–4.66
(m, 2H), 2.87 (s, 3H), 2.31 (s, 3H), 1.64 (d, 3H, J=8 Hz);
13C NMR (100 MHz, CDCl3) d 142.1, 142.0, 140.7, 133.1,
133.0, 128.8, 128.0, 127.5, 127.1, 118.5, 62.3, 52.8, 35.7, 23.8,
18.8; IR (neat) 3476, 1620, 1158 cmÀ1; HRMS (TOF) Calcd
for C17H19NO2S 301.1136; Found, 301.1140.
6-(4-Methoxyphenyl)-1,4-dimethyl-2-tosylisoindoline(4c).
1
Amorphous solid, 67 mg, 82%; H NMR (400 MHz, CDCl3)
d 7.70 (d, 2H, J=8 Hz), 7.36 (d, 2H, J=12 Hz), 7.21 (d,
2H, J=8 Hz), 7.11 (s, 1H), 6.99 (s, 1H), 6.87 (d, 2H, J=
12 Hz), 4.88 (d, 1H, J=4 Hz), 4.62 (dd, 1H, J=12 Hz,
8 Hz), 4.42 (d, 1H, J=16 Hz), 3.75 (s, 3H), 2.31 (s, 3H),
2.16 (s, 3H), 1.63 (d, 3H, J=8 Hz); 13C NMR (100 MHz,
CDCl3) d 159.2, 143.5, 142.1, 141.3, 134.5, 133.2, 132.7, 132.4,
129.8, 128.1, 127.5, 127.3, 117.9, 114.2, 62.2, 55.3, 53.0, 24.0,
21.5, 18.7; IR (neat) 3414, 1619, 1186 cmÀ1; HRMS (TOF)
Calcd for C24H25NO3S 407.1555; Found, 407.1554.
6-(4-Methoxyphenyl)-1,4-dimethyl-2-(methylsulfonyl)-
AHCTUNGTRENNUNG
isoindoline(4i). Amorphous solid, 52 mg, 79%; 1H NMR
(400 MHz, CDCl3) d 7.49–7.46 (m, 2H), 7.27 (s, 1H), 7.15 (s,
1H), 6.96 (d, 2H, J=8 Hz), 5.08–5.04 (m, 1H), 4.69–4.61
(m, 2H), 3.84 (s, 3H), 2.86 (s, 3H), 2.30 (s, 3H), 1.63 (d, 3H,
J=8 Hz); 13C NMR (100 MHz, CDCl3) d 159.3, 142.1, 141.6,
133.2, 132.9, 132.5, 128.2, 127.6, 118.0, 114.2, 62.4, 55.4, 52.8,
Adv. Synth. Catal. 0000, 000, 0 – 0
5
ꢁ 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ÞÞ
These are not the final page numbers!