Screening of conditions and promoters for a dienamine-catalyzed asymmetric pyrone Diels–Alder reaction of 22 and 23.
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Entry | Additive | Catalyst | Yield (%) | dr | eec (%) |
1a | PhCO2Ha | 13 | 52 | 4.9 : 1 | 87 |
2 | PhCO2Hb | 20 | 56 | 5.7 : 1 | 93 |
3 | Et3Nb | 20 | 13 | 4.9 : 1 | n.d. |
4 | — | 20 | 93 | 6.7 : 1 | 94 |
5 | — | 13 | 70 | 2.3 : 1 | 90 |
6 | — | 25 | 64 | 3.5 : 1 | 92 |
7 | — | 26 | 10 | 3.0 : 1 | 20 |
8 | — | 27 | — | n.d. | n.d. |
10 mol% loading of both catalyst and benzoic acid.
0.1 equiv. added.
Measured for major diastereomer.