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. Author manuscript; available in PMC: 2012 Mar 21.
Published in final edited form as: Chemistry. 2011 Mar 1;17(13):3630–3643. doi: 10.1002/chem.201003454

Table 7.

Opening of vinyl aziridine.

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Entry Conditions Yields
1 1.5 equiv BF3•Et2O, 0.15 M in 3-pentanol, rt 31% 46, 54% 47
2 1.2 equiv BF3•Et2O, 0.15 M in 3-pentanol, −20 °C 20% 46, 41% 47
3 1.5 equiv BF3•Et2O, 0.15 M in 3-pentanol, 75 °C 60% 46, 22% 47
4 1.5 equiv In(OTf)3, 0.15 M in 3-pentanol, 75 °C 17% 46, 71% 47
5 10 mol% Cu(OTf)2, 0.1 M in 3-pentanol, 0-rt-100 °C 87% 47
6 1.5 equiv BF3•Et2O, 0.15 M in 3-pentanol, 75 °C 54% 46, 36% 47, 12% 48
7 1.5 equiv BF3•Et2O, 0.05 M in 3-pentanol, 70 °C 54% 46, 34% 47, 12% 48
8 1.5 equiv BF3•Et2O, 0.05 M in 3-pentanol, 3Å MS, 70 °C 50% 46, 34% 47, 16% 48
9 1.5 equiv B(OCHEt2)3, 0.15 M in 3-pentanol, 75 °C No reaction
10 Azeotropically dired with toluene, then 1.5 equiv BF3•Et2O, 0.15 M in 3-pentanol, 75 °C 60% 46, 26% 47, 13% 48
11 1.5 equiv BF3•Et2O, 1 equiv BSA in rxn, 0.15 M in 3-pentanol, rt 25% 46, 57% 47, 7% 48, 11% starting material
12 Pre-mixed with BSA, volatile fully removed; then 1.5 equiv BF3•Et2O, 0.15 M in 3-pentanol, 75 °C 65% 46, 20% 47, 15% 48