Development of the Formation of Enolate Controlled by Acid-base Bifunctional Organochalcogenide Catalysts
| Project/Area Number |
20590021
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kinjo Gakuin University |
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Principal Investigator |
WATANABE Shinichi Kinjo Gakuin University, 薬学部, 准教授 (40275095)
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| Project Period (FY) |
2008 – 2010
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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | 不斉反応 / 光学活性スルフィド / 光学活性セレニド / 光学活性テルリド / オキシラン / シクロプロパン / アジリジン / セレノニウム塩 / 光学活性テルラン / 不斉触媒 / 不斉シクロプロパン化 / 不斉アジリジン化 / ヘテロ原子化学 / 合成化学 / セレニド / ホスフィン / ジアステレオ選択性 / スルフィド |
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| Research Abstract |
Asymmetric cyclopropanation, epoxidation and aziridination catalyzed by chiral chalcogenides are described. A novel Lewis acid/Bronsted base catalysts formed by a C2 symmetric chiral chalcogenide bearing isoborneol or camphor skeletons were readily prepared from (1S)-10-camphorsulfonic acid. Di-exo-2-hydroxy-10- bornyl selenide and LiH promoted the reaction of phenacyl bromide with methyl vinyl ketone to afford the desired trans cyclopropane with up to 50% ee. The reaction of phenacyl bromide with N-benzylidene-4-methylbenzenesulfonamide was also catalyzed by the selenide to produce the cis aziridine with up to 60% ee. Although the good yields and moderate enantioselectivities for oxirane formations were obtained from the reaction of phenacyl bromide with aromatic aldehydes, the reactions with aliphatic aldehydes afforded the desired epoxides in good yields and poor enantioselectivities.
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Report
(4 results)
Research Products
(6 results)
