Catalytic Asymmetric Synthesis and Properties of Fluorinated b2-Amino Acids
| Project/Area Number |
16K18856
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Microbial Chemistry Research Foundation |
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Principal Investigator |
NODA Hidetoshi 公益財団法人微生物化学研究会, 微生物化学研究所, 研究員 (40771738)
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| Project Period (FY) |
2016-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2016: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | 不斉触媒 / β-アミノ酸 / ペプチド / 不斉合成 / 触媒的不斉合成 / 含フッ素アミノ酸 |
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| Outline of Final Research Achievements |
This research project aimed at catalytic asymmetric synthesis of beta2-amino acids. Cyclic hydroxylamines were selected as a surrogate for beta-alanine, and used as substrates in the catalytic reactions. Two new catalytic asymmetric transformations have been developed for the synthesis of the building block molecules. One is a Pd-catalyzed decarboxylative allylation, and the other an organocatalytic direct Mannich-type reaction to ketimines. Both transformations produced the corresponding products in highly stereoselective fashion, which were readily converted to beta-amino acid derivatives otherwise difficult to access. Moreover, the products were easily implemented into the standard Fmoc-based solid phase peptide synthesis protocol, providing alpha/beta-hybrid peptides. Beta-Amino acids obtained in this project would find a specific utility in broad chemical areas such as medicinal chemistry and agrochemistry.
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Report
(3 results)
Research Products
(35 results)
