Table 1.
Entry | Conditions | Yield |
---|---|---|
1a | 10% Pd(OAc)2, 2 equiv. CuCl2, 2 equiv. NaHCO3, MeCN, RT, 1 h | 5% |
2a | 3 equiv. tBuOCl, DCM, RT, 2 h | <5% |
3a | 2 equiv. NIS, 4 equiv. NaHCO3, MeCN, 0 °C, 0.5 h | 52% (dr 5:1) |
4a | 3 equiv. I2, 4 equiv. NaHCO3, MeCN, RT, 1 h | 56% |
5a | 3 equiv. I2, 4 equiv. NaHCO3, MeCN, 0 °C, 1 h | 65% (dr 5:1) |
6b | 3 equiv. I2, 4 equiv. NaHCO3, THF, 0 °C, 1 h | 71% (dr > 15:1) |
7c | 3 equiv. I2, 4 equiv. NaHCO3, MeCN, 0 °C, 1 h | 61% (dr > 15:1) |
aR1 = Phth, R2 = Boc
bR1 = Fmoc, R2 = Cbz
cR1 = Boc, R2 = Cbz