Table 2.
Entry | Enallene | Carbocycle | Time [h] | Yield [%][b] | ee [%][c] |
---|---|---|---|---|---|
1 | 42 | 93 | 84 | ||
2 | 42 | 88 | 84 | ||
3 | 84 | 79 | 93 | ||
4 | 72 | 83 | 92 | ||
5 | 72 | 68 | 92 | ||
6 | 96 | 86 | 88 | ||
7 | 96 | 34 | 51 | ||
8 | 48 | 75 | 71 | ||
9 | 96 | 79 | 75 | ||
10 | 48 | 0 | –[d] | ||
11 | 86 | 10 | 68 | ||
12 | 48 | 0 | –[d] | ||
13 | 108 | 76 | 93 |
Reaction conditions: Enallene (0.2 mmol), Pd(OAc)2 (5 mol %), 4 a (10 mol %), B2pin2 (1.0 equiv), and BQ (1.5 equiv) in anhydrous m-xylene (1.0 mL) under argon at 13 °C.
Yields of isolated products after column chromatography.
Determined by HPLC on a chiral stationary phase.
Not determined. E=CO2Me, Ts=para-toluenesulfonyl.