Regiospecific Synthesis of Tetra-Substituted Furans
Sydnes, LK; Isanov, R; Sengee, M; Livi, F
| HERO ID | 4936186 |
|---|---|
| In Press | No |
| Year | 2013 |
| Title | Regiospecific Synthesis of Tetra-Substituted Furans |
| Authors | Sydnes, LK; Isanov, R; Sengee, M; Livi, F |
| Journal | Synthetic Communications |
| Volume | 43 |
| Issue | 21 |
| Page Numbers | 2898-2905 |
| Abstract | alpha,beta-Unsaturated acetylenic -hydroxyketones have been shown to react with ethyl acetoacetate in a Michael-addition fashion and subsequently undergo cyclization followed by dehydration to give substituted furans with a predictable regiospecificity. The yields were good to excellent. A mechanism for the transformation is proposed, and this mechanism explains why furan formation does not take place when the same unsaturated ketones are treated with -methylated acetoacetate and diethyl malonate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.] |
| Doi | 10.1080/00397911.2012.748076 |
| Wosid | WOS:000322307500009 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Keyword | Conjugated acetylenic ketones; ketoesters; propargylic alcohols |