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. Author manuscript; available in PMC: 2015 Dec 1.
Published in final edited form as: Chem Sci. 2014 Aug 27;5(12):4840–4844. doi: 10.1039/C4SC01327A

Table 2.

Enantioselective Synthesis of Tetrahydroquinolines.a

graphic file with name nihms-622908-f0005.jpg
Entry Substrate R1–X Product Yield (%)b er
1 1e p-tBu-C6H4–Br 2e 95 95:5
2 1e graphic file with name nihms-622908-t0006.jpg 2f 87 95:5
3 1e p-MeO-C6H4–Br 2g 88 95:5
4 1e p-CF3-C6H4–Br 2h 89 94:6
5 1e m-CF3-C6H4–Br 2i 94 92:8
6 1e p-PhC(O)C6H4–Br 2j 82 96:4
7 1e graphic file with name nihms-622908-t0007.jpg 2k 86 95:5
8 1e graphic file with name nihms-622908-t0008.jpg 2l 98 95:5
9 1e graphic file with name nihms-622908-t0009.jpg 2m 91 95:5
10 1b p-tBu-C6H4–Br 2b 86 92:8
11 1b p-tBu-C6H4-I 2b 85 92:8
12 1b graphic file with name nihms-622908-t0010.jpg 2n 81 94:6
13 1b p-Cl-C6H4–Br 2o 81 89:11
14 1b p-PhC(O)C6H4–Br 2p 82 95:5
15c 1b p-PhC(O)C6H4–Br 2p 77 94:6
16 1b graphic file with name nihms-622908-t0011.jpg 2q 96 95:5
17 1b graphic file with name nihms-622908-t0012.jpg 2r 83 96:4
18 1h Ph–Br 2s 86 75:25
19 1i Ph–Br – NRd
20 1j Ph–Br – NRd
a

Conditions: 1.0 equiv 1b or 1e, 2.0 equiv R-X, 2.0 equiv NaOtBu, 2 mol % Pd2(dba)3, 6 mol % (S)-Siphos-PE, xylenes or toluene (0.1 M), 90 °C (substrate 1b) or 125 °C (substrate 1e), 12-14 h.

b

Isolated yield (average of two or more runs).

c

The reaction was conducted with 1.1 equiv ArX, 1.1 equiv NaOtBu, 1 mol % Pd2(dba)3, 3 mol % (S)-Siphos-PE, toluene (0.2 M), 90 °C, on a 1mmol scale.

d

No reaction was observed.