Table 2.
Scope of Pivalatea
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---|---|---|---|---|---|
entry | 1 (% ee)b | Product | yield (%)c | ee (%)d | es (%)e |
1f,g |
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71 | 94 | ≥94 |
2g |
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93 | 97 | ≥97 |
3g |
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94 | 96 | ≥96 |
4h |
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72 | 91 | 98 |
5f,i |
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85 | 86 | ≥86 |
6f,i,j |
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96 | 80 | ≥80 |
7k |
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87 | 93 | ≥93 |
8 |
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84 | 94 | 96 |
9 |
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45 | 89 | 94 |
10 |
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73 | 73 | 85 |
11 |
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94 | 58 | 71 |
12l,m |
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49 | 72 | 88 |
13m,n |
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33 | 84 | 90 |
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.
Determined by chiral HPLC.
Average isolated yield of duplicate experiments (±0–2%), unless otherwise noted.
Determined by chiral HPLC. Average ee of duplicate experiments reported (±0–1%).
% es = enantiospecificity = (prod ee)/(SM ee)*100.
10 mol % Ni(cod)2.
80 °C.
12 h.
90 °C.
Result of a single experiment.
50 °C.
32 °C.
24 h.
100 °C.