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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 3.

Enantioselective Synthesis of Tetrahydroquinoxalinesa

graphic file with name nihms-622908-f0013.jpg
Entry Substrate R1–X Product Yield (%)b er
1 3a Ph–Br 4a 79 97:3
2 3a p-PhC(O)-C6H4-Br 4b 78 96:4
3 3a graphic file with name nihms-622908-t0014.jpg 4c 84 93:7
4 3a graphic file with name nihms-622908-t0015.jpg 4d 82 96:4
5c 3a graphic file with name nihms-622908-t0016.jpg 4e 70 93:7
6 3a graphic file with name nihms-622908-t0017.jpg 4f 74 98:2
7 3b Ph–Br 4g 79 96:4
8 3c Ph–Br NR
a

Conditions: 1.0 equiv 3, 2.0 equiv R–X, 2.0 equiv NaOtBu, 2 mol % Pd2(dba)3, 6 mol % (S)-Siphos-PE, toluene (0.1 M), 110 °C, 12-14 h.

b

Isolated yield (average of two or more runs).

c

The reaction was conducted at 120 °C in xylenes.

d No reaction was observed.