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Optimization of Methyl Propiolate Addition to Octanal.
| entry | X/Y | conditions | yield[a] | ee[b] |
|---|---|---|---|---|
|
| ||||
| 1 | 2.8/2.95 | - | 62% | 92% |
| 2 | 1.5/1.5 | - | 37% | 86% |
| 3 | 1.5/1.5 | 20 mol % TPPO |
35% | 90% |
| 4 | 1.2/1.5 | - | 42% | 91% |
| 5 | 2.8/2.95 (Et2Zn) |
4 h alkyne premix |
60% | 70% |
| 6 | 1.2/1.5 | 20 mol % (S,S)-1 |
57% | 90% |
| 7 | 2.8/2.95 | 20 mol % (S,S)-1 |
72% | 87% |
All reactions were run on a 0.325 mmol scale. Isolated yield.
Enantiomeric excess determined by chiral HPLC analysis.
