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|
| Type |
Poster Presentation |
| Area |
Organic Chemistry |
| Room No. |
Event Hall |
| Time |
4월 19일 (목요일) 11:00~12:30 |
| Code |
ORGN.P-566 |
| Subject |
Synthesis of Chiral 3,4-Dihydropyranones through Bioinspired Michael addition/lactonization Reaction Cascade |
| Authors |
HUI JIN, JUYEOL LEE, Do Hyun Ryu*
Department of Chemistry, Sungkyunkwan University, Korea
|
| Abstract |
Dihydropyranones are important structural core of numerous natural or synthetic biologically active compounds. A biomimetic tandem Michael addition-lactonization reaction of thioesters and β,γ-unsaturated α-Keto esters catalyzed by proline derived urea catalyst has been developed for the synthesis of chiral 3,4-dihydropyranones. The reaction provided 3-thioester-substituted 3,4-dihydropyranones and spiro-3,4-dihydrocoumarin-fused 3′,4′-dihydropyranones in high yield (up to 94%) with excellent stereoselectivities (up to >20:1 dr, 99% ee). The high level of stereoselectivities were rationalized by DFT calculations. In addition, the utility of the products was shown in the formal synthesis of anti-hypercholesterolemic agent. |
| E-mail |
jinhui_1989@126.com |
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121st General Meeting of the KCS