Development of a new acid-base bifunctional asymmetric organocatalyst and its utilization
| Project/Area Number |
24659009
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagasaki University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | 不斉合成 / 有機触媒 / 有機合成化学 / 酸ー塩基複合型触媒 / 不斉反応 / キニーネ / α-イソクプレイン / β-イソクプレイジン |
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| Research Abstract |
beta-ICD is the versatile catalyst utilized for various organocatalytic asymmetric reactions represented by the Morita-Baylis-Hillman (MBH) reaction. However, the enantiomer of beta-ICD is not easily available. In this research we have developed a new cinchona alkaloid-derived catalyst, alpha-ICPN, which is available in 90% yield in one step from quinine. alpha-ICPN effectively catalyzed MBH reactions in high and opposite enantioselectivity to that observed for the beta-ICD-catalyzed reactions. In addition, one derivative of alpha-ICPN catalyzed aza-version of MBH reactions in high enantioselectivity. These results suggest that alpha-ICPN can be utilized as an enantiocomplementary catalyst of beta-ICD. Furthermore, we have developed a new methodology for the construction of polypropionate structures by taking advantage of both beta-ICD and alpha-ICPN-catalyzed MBH reactions.
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Report
(3 results)
Research Products
(28 results)
