2011 Fiscal Year Final Research Report
Development of Dynamic Asymmetric Organocatalysis and Their Mechanistic Studies
| Project/Area Number |
22750084
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | The Institute of Physical and Chemical Research (2011)
Tokyo University of Agriculture and Technology (2010) |
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Principal Investigator |
SOHTOME Yoshihiro 独立行政法人理化学研究所, 袖岡有機合成化学研究室, 研究員 (50431888)
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| Project Period (FY) |
2010 – 2011
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| Keywords | 有機触媒 / 不斉合成 / 水素結合 / エントロピー / マイケル反応 / フェノール |
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| Research Abstract |
We have designed and developed 1, 3-diamine-tethered guanidine/bisthiourea organocatalysts for catalytic asymmetric 1, 4-additions including 1) Friedel-Crafts alkylation of phenols and 2) phospha-Michael reactions. Kinetic analyses using Eyring plots uncovered that differences in the activation entropies(ΔΔS^‡) play a principal role in the stereodiscrimination of the developed F-C reactions. We also found that, in the phospha-Michael reactions, either the monomeric or oligomeric active species of the catalyst can be utilized depending on the solvent system.
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