書誌事項
- タイトル別名
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- Development and Application of Enantioselective Lewis Acid-Lewis Base Bifunctional Catalyst.
- ルイスサン ルイス エンキ フクゴウ タテン ニンシキ フセイ ショクバイ ノ ソウセイ ト テンカイ
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The design, synthesis, and application of a new bifunctional enantioselective catalyst, containing both Lewis acidity and Lewis basicity, are described. The catalysts are composed of a Lewis acid metal (aluminum or titanium) and a Lewis base (the oxygen atom of a phosphine oxide), of which positions are defined by BINOL or carbohydrate scaffold. Utilizing these catalysts, we have developed a variety of enantioselective cyanation reactions, such as cyanosilylation of aldehydes and ketones, Strecker-type reaction, and Reissert-type reaction. These reactions showed a broad sub-strate generality. Investigations toward elucidation of the reaction mechanism, involving kinetic studies, comparison with results by control catalysts, and absolute configurations of the products, revealed that these reactions are catalyzed by a dual activation of a substrate and TMSCN by the Lewis acid and the Lewis base of these catalysts. Catalytic enantioselective total synthesis of anticancer epothilones and a potent NMDA receptor antagonist was achieved, using these reactions as key steps.
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 59 (8), 766-778, 2001
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
- 1390001205277882112
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- NII論文ID
- 10012287587
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 5867100
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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
- Crossref
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- 抄録ライセンスフラグ
- 使用不可