Abstract
The condensation reaction of a γ-tert-butylallenoate, ethyl 5,5-dimethylhexa-2,3-dienoate, and aldehydes in the presence of sodium ethoxide is described. A range of aldehydes readily reacts with γ-tert- butylallenoate and ethoxide providing a straightforward synthesis of 1,2,3,4-tetrasubstituted conjugated dienes in moderate to good yields and exclusive E,E selectivity. For some aldehydes, the condensation chemoselectively delivers conjugated enynes in good yields and exclusive E selectivity.
| Original language | English |
|---|---|
| Article number | SS-2014-H0176-OP |
| Pages (from-to) | 2085-2092 |
| Number of pages | 8 |
| Journal | Synthesis |
| Volume | 46 |
| Issue number | 15 |
| DOIs | |
| State | Published - Aug 2014 |
Keywords
- allenoate
- condensation
- conjugated diene
- enyne
- tandem reaction
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