乙甲的林催化曼尼赫反应
Jung Woon Yang1, Carley Chandler, Michael Stadler
1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany.
Nature
|February 22, 2008
概括
小的有机分子,如,是有效的不对称的催化剂. 这项研究证明了乙甲.
科学领域:
- 不对称的催化剂.
- 有机化学 有机化学
- 绿色化学 绿色化学
背景情况:
- 小有机分子,如普罗林,是不对称催化剂的关键类别,补充酶和金属复合物.
- 这些催化剂通过核性酶胺中间体激活碳化合物,使性分子的合成成为可能.
- 在不对称催化中直接使用乙甲,一个简单的二碳核,仍然是一个重大挑战.
研究的目的:
- 为了证明乙甲作为核友在不对称的,素催化曼尼赫反应中的实用性.
- 通过使用乙烯基合成具有高反选择性的有价值的β-氨基 aldehydes.
- 在小分子催化中将乙乙作为一种多功能且实用的双碳核.
主要方法:
- 开发了不对称的,以素催化的曼尼赫反应,利用乙甲作为核爱体.
- 乙甲与N-tert-butoxycarbonyl (N-Boc) -imines. 的反应
- 对反应产物的反选择性和产量的分析.
主要成果:
- 乙甲基被成功地用作在不对称的,素催化曼尼赫反应中的强大的核爱体.
- 这些反应产生了具有极高酶选择活性的β-氨基 aldehydes.
- 证明了乙甲在合成药物中间体和其他生物活性分子中的实用用途.
结论:
- 这项研究克服了在不对称小分子催化中使用乙甲的挑战.
- 开发的方法提供了一条通用且具有成本效益的途径,以获得有价值的性构建块.
- 这些发现为药物发现和合成的实际应用开辟了新的途径.
相关概念视频
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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
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