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. 2015 Mar 24;54(20):6024–6027. doi: 10.1002/anie.201501048

Table 2.

Scope of the enantioselective carbocyclization–borylation reaction.[a]

Entry Enallene Carbocycle Time [h] Yield [%][b] ee [%][c]
1 Inline graphic Inline graphic 42 93 84
2 Inline graphic Inline graphic 42 88 84
3 Inline graphic Inline graphic 84 79 93
4 Inline graphic Inline graphic 72 83 92
5 Inline graphic Inline graphic 72 68 92
6 Inline graphic Inline graphic 96 86 88
7 Inline graphic Inline graphic 96 34 51
8 Inline graphic Inline graphic 48 75 71
9 Inline graphic Inline graphic 96 79 75
10 Inline graphic Inline graphic 48 0 [d]
11 Inline graphic Inline graphic 86 10 68
12 Inline graphic Inline graphic 48 0 [d]
13 Inline graphic Inline graphic 108 76 93
[a]

 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.

[b]

 Yields of isolated products after column chromatography.

[c]

 Determined by HPLC on a chiral stationary phase.

[d]

 Not determined. E=CO2Me, Ts=para-toluenesulfonyl.