Table 2. Different Amines for the Asymmetric α-Allylation of 1a.
| entrya | amine | yield (%)b | ee (%)c |
|---|---|---|---|
| 1 | A1 | 89 | 31 (S) |
| 2 | (R,R)-A2 | 98 | 94 (R) |
| 3 | (S,S)-A2 | 97 | 94 (S) |
| 4 | A3 | 89 | 37 (R) |
| 5 | A4 | 89 | 21 (R) |
| 6 | A5 | 90 | 60 (R) |
| 7 | A6 | 97 | 44 (R) |
Performed on a 0.375 mmol scale by using 4.0 mol % Pd(PPh3)4, 50 mol % amine, 6.25 mol % P5, 190 mg 5 Å molecular sieves, and 0.75 mmol allyl alcohol in 0.75 mL MTBE at 60 °C for 16 h.
Determined by GC analysis.
Determined by chiral HPLC analysis using a Diacel Chiralcel AS-H column. Absolute configurations were determined by measuring the optical rotations and comparing with the literature data.
