2
062
J. Wu et al.
LETTER
(
3) (a) Murahashi, S. I.; Imada, Y.; Hirai, Y. Tetrahedron Lett.
987, 28, 77. (b) Murahashi, S. I.; Imada, Y.; Hirai, Y. Bull.
Hz, 1 H), 7.13–7.22 (m, 4 H), 7.33–7.49 (m, 5 H) ppm.
1
3
1
C NMR (75 MHz, CDCl ): d = 19.7, 27.4, 43.8, 56.2, 58.2,
3
Chem. Soc. Jpn. 1989, 62, 2968.
125.6, 125.8, 126.8, 127.4, 128.2, 128.7, 128.8, 134.3,
(4) For the reviews of the transfer hydrogenation, see:
139.5, 140.4 ppm. HRMS (ESI): m/z calcd for C H N
1
7
19
(
(
a) Brieger, G.; Nestrick, T. J. Chem. Rev. 1974, 74, 567.
b) Johnstone, R. A. W.; Wilby, A. H.; Entwistle, I. D.
[M + H]: 238.1590; found: 238.1593.
Compound 2c: colorless oil. IR: 3058, 3024, 2991, 2930,
–
1
Chem. Rev. 1985, 85, 129. (c) Noyori, R.; Hashiguchi, S.
Acc. Chem. Res. 1997, 30, 97. (d) Gladiali, S.; Alberico, E.
Chem. Soc. Rev. 2006, 35, 226.
2867, 2830, 2803, 1607, 1513, 1492, 1462, 1353, 741 cm .
1
H NMR (300 MHz, CDCl ): d = 1.20 (d, J = 6.4 Hz, 3 H),
3
2.66 (dd, J = 5.8, 16.2 Hz, 1 H), 3.03–3.20 (m, 2 H), 3.62 (d,
J = 13.2 Hz, 1 H), 3.66 (d, J = 15.7 Hz, 1 H), 3.75 (d,
J = 15.8 Hz, 1 H), 3.87 (d, J = 13.2 Hz, 1 H), 6.90–7.00 (m,
1 H), 7.12–7.15 (m, 3 H), 7.29–7.44 (m, 5 H) ppm. 1 C NMR
(
(
(
5) Fujita, K.; Kitatsuji, C.; Fulukawa, S.; Yamaguchi, R.
Tetrahedron Lett. 2004, 45, 3215.
6) Frediani, P.; Rosi, L.; Cetarini, L.; Frediani, M. Inorg. Chim.
Acta 2006, 359, 2650.
7) (a) No product was observed when isoquinoline was
refluxed in MeCN catalyzed by [Cp*RhCl ] with 5:2 formic
3
(75 MHz, CDCl ): d = 15.1, 35.5, 51.5, 52.1, 57.2, 125.5,
3
126.0, 126.4, 126.9, 128.2, 128.8, 128.9, 134.0, 134.4, 139.4
ppm. HRMS (ESI): m/z calcd for C H N [M + H]:
2
2
17 19
acid–Et N azeotropic mixture. (b) Watanabe, Y.; Ohta, T.;
238.1590; found: 238.1579.
3
Tsuji, T.; Hiyoshi, T.; Tsuji, T. Bull. Chem. Soc. Jpn. 1984,
Compound 2e: yellow oil. IR: 2921, 2832, 1610, 1575, 1524,
1452, 1465, 821, 800, 771, 733, 699 cm . H NMR (300
–
1 1
5
7, 2440.
8) (a) Balczewski, P.; Joule, J. A. Synth. Commun. 1990, 20,
815. (b) Derdau, V. Tetrahedron Lett. 2004, 45, 8889.
c) Zacharie, B.; Moreau, N.; Dockendorff, C. J. Org. Chem.
001, 66, 5264.
(
MHz, CDCl ): d = 2.76 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9
3
2
(
2
Hz, 2 H), 3.69 (s, 2 H), 3.70 (s, 2 H), 7.24–7.26 (m, 2 H),
1
3
7.29–7.41 (m, 5 H), 7.80–7.83 (m, 1 H) ppm. C NMR (75
MHz, CDCl ): d = 27.2, 49.9, 56.0, 62.5, 122.8, 126.1,
3
(
9) (a) Xue, D.; Chen, Y. C.; Cui, X.; Wang, Q. W.; Zhu, J.;
Deng, J. G. J. Org. Chem. 2005, 70, 3584. (b) Ma, Y.; Liu,
H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. Org. Lett. 2003, 5,
127.4, 128.4, 129.0, 130.3, 131.7, 137.6, 138.0 ppm. HRMS
(ESI): m/z calcd for C H N O [M + H]: 269.1285; found:
1
6
17
2
2
269.1281.
Compound 2g: light yellow oil. IR: 3058, 3024, 2991, 2929,
2103. (c) Wang, F.; Liu, H.; Cun, L.; Zhu, J.; Deng, J.; Jiang,
–
1 1
Y. J. Org. Chem. 2005, 70, 9424. (d) Liu, W.; Cui, X.; Cun,
L.; Wu, J.; Zhu, J.; Deng, J. Tetrahedron: Asymmetry 2005,
2867, 2830, 1607, 1513, 1492, 1462, 730 cm . H NMR
(300 MHz, CDCl ): d = 0.96 (t, J = 7.3 Hz, 3 H), 1.73–1.79
3
16, 2525. (e) Chen, Y. C.; Wu, T. F.; Deng, J. G.; Liu, H.;
(m, 2 H), 2.46–2.54 (m, 1 H), 2.73–2.84 (m, 2 H), 3.13–3.18
(m, 1 H), 3.46 (t, J = 6.2 Hz, 1 H), 3.69 (d, J = 13.5 Hz, 1 H),
3.80 (d, J = 13.5 Hz, 1 H), 3.85 (s, 3 H), 3.87 (s, 3 H), 6.54
Cui, X.; Jiang, Y. Z.; Choi, M. C. K.; Chan, A. S. C. J. Org.
Chem. 2002, 67, 5301. (f) Chen, Y.; Wu, T.; Jiang, L.;
Deng, J.; Liu, H.; Zhu, J.; Jiang, Y. J. Org. Chem. 2005, 70,
1
3
(s, 1 H), 6.59 (s, 1 H), 7.24–7.41 (m, 5 H) ppm. C NMR (75
1
006.
MHz, CDCl ): d = 10.9, 24.2, 29.0, 43.6, 55.7, 55.9, 57.8,
3
(
(
10) Wu, J.; Wang, F.; Ma, Y.; Cui, X.; Cun, L.; Zhu, J.; Deng, J.;
Yu, B. Chem. Commun. 2006, 1766.
61.9, 110.6, 111.2, 126.5, 126.7, 128.1, 128.8, 130.6, 140.0,
147.1 ppm. HRMS (ESI): m/z calcd for C H NO [M + H]:
2
0
25
2
11) (a) Karimov, A.; Levkovich, M. G.; Abdullaev, N. D.;
Shakirov, R. Chem. Nat. Compd. 1994, 30, 331.
312.1958; found: 312.1968.
Compound 2h: light yellow oil. IR: 2950, 2904, 2867, 2831,
1608, 1513, 1463, 1375, 1358, 770 cm . H NMR (300
–
1 1
(
3
b) Karimov, A.; Shakirov, R. Chem. Nat. Compd. 1994, 30,
35.
MHz, CDCl ): d = 0.85 (d, J = 6.8 Hz, 3 H), 0.98 (d, J = 6.8
3
(
12) General Procedure.
Hz, 3 H), 1.85–1.92 (m, 1 H), 2.42 (s, 3 H), 2.57–2.69 (m, 3
H), 3.09–3.17 (m, 2 H), 3.82 (s, 3 H), 3.83 (s, 3 H), 6.53 (s,
To a solution of 1 (0.5 mmol) and [Cp*RhCl ] (0.0025
2
2
1
3
mmol) in CH Cl (1.5 mL) under an atmosphere of argon
1 H), 6.56 (s, 1 H) ppm. C NMR (75 MHz, CDCl3):
d = 20.0, 20.1, 25.4, 34.3, 44.1, 48.2, 55.7, 55.8, 69.4, 111.0,
111.8, 127.4, 128.7, 146.3, 147.0 ppm. HRMS (ESI): m/z
calcd for C H NO [M + H]: 250.1802; found: 250.1805.
2
2
was added a 5:2 formic acid–Et N azeotropic mixture (0.125
3
mL). The resulting mixture was stirred at 40 °C for a certain
period of time, made basic by addition of aq Na CO , and
2
3
15 24
2
then extracted with CH Cl . Purification on silicon gel
Compound 2i: white solid; mp: 80–81 °C. IR: 3022, 2946,
2
2
afforded the desired products 2, which were characterized by
H NMR, C NMR and IR spectroscopy, and HRMS. The
data of unknown compounds was shown as the following:
2907, 2832, 1607, 1513, 1488, 1463, 1451, 1364, 741, 716
1
13
–1 1
cm . H NMR (300 MHz, CDCl ): d = 2.24 (s, 3 H), 2.57–
3
2.65 (m, 1 H), 2.71–2.78 (m, 1 H), 3.06–3.22 (m, 2 H), 3.56
(s, 3 H), 3.85 (s, 3 H), 4.18 (s, 1 H), 6.09 (s, 1 H), 6.60 (s, 1
Compound 2a: colorless oil. IR: 3061, 3024, 2916, 2799,
–
1
1
13
1
602, 1495, 1464, 1453, 739 cm . H NMR (300 MHz,
H), 7.22–7.34 (m, 5 H) ppm. C NMR (75 MHz, CDCl3):
CDCl ): d = 2.80 (t, J = 5.9 Hz, 2 H), 2.96 (t, J = 5.8 Hz, 2
d = 28.9, 44.2, 52.2, 55.7, 71.0, 110.6, 111.4, 126.5, 127.3,
128.2, 129.5, 130.3, 143.8, 147.0, 147.3 ppm. HRMS (ESI):
m/z calcd for C H NO [M + H]: 284.1645; found:
3
H), 3.70 (s, 2 H), 3.74 (br s, 2 H), 7.04 (br s, 1 H), 7.12–7.17
1
3
(
m, 3 H), 7.31–7.47 (m, 5 H) ppm. C NMR (75 MHz,
1
8
22
2
CDCl ): d = 29.1, 50.6, 56.1, 62.7, 125.5, 126.0, 126.5,
284.1639.
Compound 2k: light yellow oil. IR: 3024, 2964, 2918, 2838,
1588, 1494, 1454, 1443, 1370, 735 cm . H NMR (300
3
1
27.0, 128.2, 128.6, 129.0, 134.3, 134.8, 138.3 ppm. HRMS
–
1 1
(
ESI): m/z calcd for C H N [M + H]: 224.1434; found:
1
6
17
2
24.1443.
MHz, CDCl ): d = 1.17 (d, J = 6.1 Hz, 3 H), 2.42 (s, 3 H),
3
Compound 2b: colorless oil. IR: 3061, 3024, 2968, 2925,
2.61–2.72 (m, 2 H), 2.80–2.88 (m, 1 H), 3.57 (d, J = 15.4 Hz,
1 H), 3.83 (d, J = 15.4 Hz, 1 H), 7.00–7.15 (m, 4 H) ppm.
–
1 1
2804, 1603, 1582, 1493, 1452, 1365, 757 cm . H NMR
1
3
(
(
300 MHz, CDCl ): d = 1.48 (d, J = 6.7 Hz, 3 H), 2.74–2.83
C NMR (75 MHz, CDCl ): d = 17.9, 36.7, 41.4, 54.8, 57.2,
3
3
m, 2 H), 2.91–3.06 (m, 1 H), 3.13–3.16 (m, 1 H), 3.78 (d,
125.5, 126.0, 128.4, 134.0, 134.4 ppm. HRMS (ESI): m/z
J = 13.6 Hz, 1 H), 3.90 (d, J = 13.6 Hz, 1 H), 3.97 (q, J = 6.7
calcd for C H N [M + H]: 162.1277; found: 162.1282.
1
1
15
Synlett 2006, No. 13, 2059–2062 © Thieme Stuttgart · New York