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- 杉村 高志
- 姫路工業大学大学院理学研究科
書誌事項
- タイトル別名
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- Chiral Tethered Reaction and Entropy-Driven Asymmetric Synthesis
- キラル カキョウ ハンノウ ト エントロピー クドウ フセイ ゴウセイ
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抄録
The 2, 4-pentanediol (PD) -tethered reaction is a stereocontrolled reaction having versatile applicability. When reactant and reagent elements are connected through a PD tether prior to their reaction, stereochemical purity of the product is very high for nine different types of reactions so far studied. Selectivity of one of the reactions shows temperature independency in a wide range from -78 to 150°C, which indicates that the selectivity is governed by the entropy term. The strict stereocontrol at the high reaction temperature can be extended to vapor phase reaction performed above 250 °C. To understand how the two methyl groups on the PD tether stereocontrol the reaction, a new parameter, chiral perturbation factor, is introduced. By this analysis, it is disclosed that the methyl groups do not promote large activation enthalpy change for both diastereomeric processes. In contrast, change in the activation entropy is large and in opposite sing, which should be an origin of the strict stereocontrol by the PD tether.
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 61 (10), 984-991, 2003
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205310979072
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- NII論文ID
- 10011908082
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 6730900
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- 抄録ライセンスフラグ
- 使用不可