Table 1. Reaction Conditions for the C–H Olefination of (±)-16.
entry | temp. (°C) | x | time (h) | 1H NMR yielda |
---|---|---|---|---|
1 | 80 | 1.5 | 16 | 49% |
2 | 60 | 1.5 | 16 | 31% |
3 | 80 | 1.5 | 6 | 45% |
4 | 80 | 1.0 | 16 | 42% |
5 | 80 | 2.0 | 16 | 54% (59%b,c+ 5%b,d) |
6e | 80 | 1.5 | 16 | 55% |
1H NMR yield of the desired regioisomer was determined by using CH2Br2 as the internal standard.
Isolated yield.
Regioselectivity was determined from the crude mixture: A/B = 6:1.
Diolefinated product.
15 mol % of Pd(OAc)2 and S,O-ligand were used.