Development of Direct Catalytic Synthesis of Primary Amine Containing Chiral Tetrasubstituted Carbon Using Unprotected Ketimine
| Project/Area Number |
17H03972
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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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 | Kyushu University |
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Principal Investigator |
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000)
Fiscal Year 2019: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2018: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥9,620,000 (Direct Cost: ¥7,400,000、Indirect Cost: ¥2,220,000)
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| Keywords | 無保護ケチミン / 不斉四置換炭素含有第一級アミン / 非天然アミノ酸 / 直接的触媒反応 / one-pot連続反応 / N無保護ケチミン / 非天然α-アミノ酸 |
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| Outline of Final Research Achievements |
To develop an environmentally friendly synthetic process for optically active primary amines containing chiral tetra-substituted carbons, we researched to create next-generation direct catalytic reactions using unprotected ketimine as a substrate.
After three years of research, we succeeded in developing the alkynylation reaction, the Mannich type reaction, the Friedel-Crafts type reaction, the decarboxylative Mannich reaction, and the Arylation reaction using Ar boronic acid, and the target compounds were obtained in high yield with high enantioselectivity. Moreover, we succeeded in developing a new environmentally friendly synthetic method, which can directly and catalytically synthesize unprotected ketimines from the corresponding ketones. We also succeeded in one-pot continuous reactions from ketones to primary amines.
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| Academic Significance and Societal Importance of the Research Achievements |
医薬品などの重要機能性分子の合成に必要な不斉四置換炭素含有光学活性第一級アミンを、大量かつ地球環境に負荷をかけることなく実用的に供給する方法の開発は、「廃棄物を出しながら目的物を合成する従来の化学」から本来不必要な廃棄物を出さない「地球環境に優しいグリーンな化学」への変換に貢献するものである。
これまで反応基質として用いられてこなかった無保護ケチミンを基質に用いることで、本質的には不必要な官能基の保護・脱保護のプロセスや活性化のプロセスを排除した、次世代型の直接的触媒反応が可能となった。本研究は、基礎研究として重要なだけではなく、創薬化学、機能性材料化学の分野の発展にも大きく寄与するものである。
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Report
(4 results)
Research Products
(193 results)
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[Journal Article] Identification of candidate molecular targets of the novel antineoplastic antimitotic NP-10.2019
Author(s)
Yokoyama T., Yukuhiro M., Iwasaki Y., Tanaka C., Sankoda K., Fujiwara R., Shibuta A., Higashi T., Motoyama K., Arima H., Yoshida K., Sugimoto N., Morimoto H., Kosako H., Ohshima T. and Fujita M.
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Journal Title
Scientific Reports
Volume: 9
Issue: 1
DOI
NAID
Related Report
Peer Reviewed / Open Access
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