| 研究課題/領域番号 |
20K15966
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| 研究機関 | 公益財団法人微生物化学研究会 |
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研究代表者 |
崔 進 公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (20839120)
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| 研究期間 (年度) |
2020-04-01 – 2023-03-31
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| キーワード | vinylogous addition / chromone / atom-economy / natural product |
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| 研究実績の概要 |
In this work, a direct catalytic asymmetric vinylogous Michael-type reaction of chromones and β,γ-butenolides to afford anti-adducts with high enantioselectivity has been developed successfully. The synthetic method developed for the reaction was characterized by (1) tuning of the steric and electronic environment within the stereocontrolling transition state using (R)-3,4,5-(MeO)3-MeOBIPHEP as a chiral ligand to invert diastereoselection, and (2) improvement of the catalyst turnover by a coordinative phenoxide additive to increase the chemical yield. This method is useful for the syntheses of natural product-like libraries with high levels of stereoselectivity.
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| 現在までの達成度 (区分) |
現在までの達成度 (区分)
2: おおむね順調に進展している
理由
The current progress is generally in line with initial expectations. A novel catalytic synthetic method has been identified successfully to generate chromone lactones with high enantioselectivity (most >99% ee) and moderate diastereoselectivity (up to 7/1). An unexpected selectivity reversal of the reaction was observed. The results achieved have been published in the journal (Chem. Sci. 2020, 11, 7170.).
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| 今後の研究の推進方策 |
Although the developed synthetic method worked well for the generation of simplified chromone lactones, the synthesis of natural products using chromone substrate bearing ester group at the β position of enone remain difficult. Thus, the identification of a more robust catalytic system suitable for the sterically hindered chromone is highly desirable, and is the next work for this project.
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| 備考 |
https://www.bikaken.or.jp/
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