Table 1. Reaction of 5a with 1 or 2 Activated in situa.
entry | borane source | activator | time (h) | conversionb (%) | 9a:10ab |
---|---|---|---|---|---|
1 | 1 | I2 | 10 | 40 | 4.3:1 |
2 | 1 | I2 | 19 | >90 | 4.7:1 |
3 | 2 | I2 | 5 | >90 | 7:1c |
4 | 2 | I2 | 5 | >90 | 18:1d |
5 | 1 | TfOH | 5 | >90 | >20:1 |
A 0.1 M solution of 5 and 2 equiv of 1 or 2 at −78 °C in CH2Cl2 was treated with 2 equiv of activator, warmed to −20 °C, stirred (time), and quenched with NaOOH/MeOH·H2O.
NMR assay.
Activated at −20 °C and warmed to −10 °C.
Warmed to −10 °C.