Catalytic asymmetric hydrogenation of benzene rings
| Project/Area Number |
15K13698
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyushu University |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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| Keywords | 触媒的不斉合成 / 水素化 / ベンゼン / サリチル酸 / ロジウム / ルテニウム |
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| Outline of Final Research Achievements |
We found that a concerted catalyst system, Rh/C and chiral ruthenium complex, allowed the hydrogenation of salicylates to proceed with high stereoselectivities. Ethyl salicylate was transformed to 91% ee of ethyl trans-2-hydroxycyclohexanecarboxylate with trans/cis = 91/9. The resulting optically active cyclohexane was transformed into a compound bearing juvenile hormone activity, as follows: (1) The ester was transformed into its Weinreb amide. The Weinreb amide was treated with aryllithium to give the ketone. The ketone carbonyl was reduced to methylene through the hydrogenation with Pd/C catalyst and a Lewis acid. The alkylation of the products gave the target compound.
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Report
(3 results)
Research Products
(9 results)
