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. Author manuscript; available in PMC: 2014 Nov 3.
Published in final edited form as: J Am Chem Soc. 2013 Feb 20;135(9):3307–3310. doi: 10.1021/ja312087x

Table 2.

Scope of Pivalatea

graphic file with name nihms-449862-f0005.jpg
entry 1 (% ee)b Product yield (%)c ee (%)d es (%)e
1f,g graphic file with name nihms-449862-t0006.jpg graphic file with name nihms-449862-t0007.jpg 71 94 ≥94
2g graphic file with name nihms-449862-t0008.jpg graphic file with name nihms-449862-t0009.jpg 93 97 ≥97
3g graphic file with name nihms-449862-t0010.jpg graphic file with name nihms-449862-t0011.jpg 94 96 ≥96
4h graphic file with name nihms-449862-t0012.jpg graphic file with name nihms-449862-t0013.jpg 72 91 98
5f,i graphic file with name nihms-449862-t0014.jpg graphic file with name nihms-449862-t0015.jpg 85 86 ≥86
6f,i,j graphic file with name nihms-449862-t0016.jpg graphic file with name nihms-449862-t0017.jpg 96 80 ≥80
7k graphic file with name nihms-449862-t0018.jpg graphic file with name nihms-449862-t0019.jpg 87 93 ≥93
8 graphic file with name nihms-449862-t0020.jpg graphic file with name nihms-449862-t0021.jpg 84 94 96
9 graphic file with name nihms-449862-t0022.jpg graphic file with name nihms-449862-t0023.jpg 45 89 94
10 graphic file with name nihms-449862-t0024.jpg graphic file with name nihms-449862-t0025.jpg 73 73 85
11 graphic file with name nihms-449862-t0026.jpg graphic file with name nihms-449862-t0027.jpg 94 58 71
12l,m graphic file with name nihms-449862-t0028.jpg graphic file with name nihms-449862-t0029.jpg 49 72 88
13m,n graphic file with name nihms-449862-t0030.jpg graphic file with name nihms-449862-t0031.jpg 33 84 90
a

Conditions: pivalate (0.20 mmol, 1.0 equiv), boroxine (0.83–1.3 equiv), Ni(cod)2 (5 mol %), NaOMe (2.0 equiv), PhMe (0.4 M), 70 °C, 3 h, unless otherwise noted.

b

Determined by chiral HPLC.

c

Average isolated yield of duplicate experiments (±0–2%), unless otherwise noted.

d

Determined by chiral HPLC. Average ee of duplicate experiments reported (±0–1%).

e

% es = enantiospecificity = (prod ee)/(SM ee)*100.

f

10 mol % Ni(cod)2.

g

80 °C.

h

12 h.

i

90 °C.

j

Result of a single experiment.

k

50 °C.

l

32 °C.

m

24 h.

n

100 °C.