2013 Fiscal Year Final Research Report
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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| Keywords | 不斉合成 / 有機触媒 |
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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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