不飽和末端エポキシドとクロロヒドリンの内分子サイクロプロパネーション
David M Hodgson1, Ying Kit Chung, Irene Nuzzo
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Journal of the American Chemical Society
|March 22, 2007
まとめ
リチウム2,2,6,6-テトラメチルピペリジド (LTMP) は,エポキシドのステレオ選択性サイクロプロパネーションを可能にし,バイサイクルアルコールを生成します. 2,2,6,6-テトラメチルピペリジン (TMP) を用いた触媒的方法は,これらの貴重な化合物のスケーラブルな合成を提供します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 合成化学 合成化学とは
背景:
- 内分子サイクロプロパネーションは,有機合成における重要な反応である.
- バイサイクル化合物のステレオセレクティブ合成は,天然製品の合成に不可欠です.
研究 の 目的:
- ビサイクロ[3.1.0]ヘクサン-2-オールとビサイクロ[4.1.0]ヘプタン-2-オールを合成するための効率的でステレオ選択的な方法を開発する.
- これらのバイサイクル化合物の合成的有用性を探求するために.
主な方法:
- リチウム2,2,6,6-テトラメチルピペリジド (LTMP) 誘導による不飽和末端エポキシドの分子内サイクロプロパン化.
- Sn-Li交換/エレクトロフィールトラッピングとStilleコップリングの詳細を詳しく説明します.
- 2,2,6,6-テトラメチルピペリジン (TMP) を使用した触媒式サイクロプロパネーション.
主要な成果:
- ビサイクロ[3.1.0]ヘクサン-2-オールとビサイクロ[4.1.0]ヘプタン-2-オールの効率的かつ完全にステレオ選択的合成.
- 多種多様な代用バイサイクルサイクロプロパンの生成.
- 触媒TMPを用いたビサイクロ[3.1.0]ヘクサン-2-オール (1g-7.5kg) のスケーラブル合成.
- (+) -β-クパレノンの非対称合成における実証された有用性.
結論:
- LTMP誘発のサイクロプロパネーションは,バイサイクルアルコールへの強力な経路を提供します.
- 触媒型TMPは,バイサイクル化合物を合成するための実用的でスケーラブルな方法を提供します.
- この化学は,複雑な分子合成に価値があります.
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