直接催化不对称的曼尼赫反应用于四度碳立体中心的构建
Barry M Trost1, Tanguy Saget1, Chao-I Joey Hung1
1Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
这项研究引入了一种用于制造复杂分子的新催化方法. -催化剂使得使用α分支能有效合成四级碳立体中心.
科学领域:
- 有机化学
- 催化剂
- 立体选择合成
背景情况:
- 在药品和天然产品中普遍存在四度碳立体中心.
- 它们的立体选择性合成的有效方法在有机化学中仍然是一个挑战.
研究的目的:
- 开发一种新型的催化曼尼赫反应,用于直接构建enantio和 diastereoselective四元碳立体中心.
- 在这种转化中利用α分支子作为核友合作伙伴.
主要方法:
- 使用Zn-ProPhenol催化剂进行曼尼赫反应.
- 使用α分支作为核友.
- 研究低催化剂负载的克尺度反应条件.
主要成果:
- 实现了四级碳立体中心的直接enantio和 diastereoselective构造.
- 在低催化剂负载下 (例如,1 mol%) 证明了克尺度上的反应效率.
- 展示了进一步阐述曼尼赫引证的能力.
结论:
- Zn-ProPhenol催化曼尼赫反应提供了一个有效的复杂立体三角形的途径.
- 这种方法提供了一种可扩展和高效的方法来合成有价值的性构建块.
更多相关视频
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
相关概念视频
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
