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. Author manuscript; available in PMC: 2016 Jun 27.
Published in final edited form as: J Am Chem Soc. 2016 Apr 8;138(15):5150–5158. doi: 10.1021/jacs.6b01643

Table 3.

Dibromination Substrate Scopea

graphic file with name nihms784843u4.jpg
entry substrate product yield (%) ee (%) mol % 11
1b 16 graphic file with name nihms784843t18.jpg 75 87 15
2 18 graphic file with name nihms784843t19.jpg 82 80 20
3c 20 graphic file with name nihms784843t20.jpg 86 80 15
4c 22 graphic file with name nihms784843t21.jpg 79 86 20
5c 26 graphic file with name nihms784843t22.jpg 84 81 20
a

Conditions unless otherwise noted: 1.1 1.2 equiv NBS, 1.1 1.3 equiv BrTi(Oi-Pr)3, 15–20 mol % (R,S)-11, hexanes, −20 °C, 4–12 hours;

b

3:1 hexanes/CCl4;

c

absolute configuration unconfirmed.