乙和区域选择性铜催化1,2-甲酸的甲酸脱芳
Mukesh Pappoppula1, Kathryn L Olsen1, Devin R Ketelboeter1
1Department of Chemistry and Florida Center for Heterocyclic Compounds, University of Florida, P.O. Box 117200, Gainesville, FL 32611, United States.
这项研究引入了一种新的铜催化反应,用于从简单的原料中合成有价值的基化二. 该方法实现了高产量和优秀的立体控制,为复杂分子提供了一条新的途径.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- 氨酸衍生物是药物化学中的重要支架.
- 开发有效的皮里丁功能化的方法至关重要.
- Dearomative反应为复杂的循环结构提供了独特的途径.
研究的目的:
- 开发一种新型的铜催化氧化氧化基化的方法.
- 为了在合成2-基-1,2-二二胺的过程中实现高的区域和反抗选择性.
- 为了证明开发的方法的广泛适用性.
主要方法:
- 一种三组分反应,涉及皮里丁,终端基和甲基酸盐.
- 使用一种化铜的催化系统和一种性双P,N-连接体 (StackPhos).
- 针对产量,区域选择性和酶选择性的反应条件的优化.
主要成果:
- 获得了高产量 (高达99%) 和优异的抗选择性 (高达99% ee).
- 对于所需的1,2-添加产品,观察到高达25:1的区域选择性比率.
- 反应能容忍终端基上广泛的功能组,包括乙气.
结论:
- 已经建立了一种多功能且高效的铜催化方法,用于对2-基-1,2-二二二烯酸的酶选择性合成.
- 该方法提供了对合成价值的性构建块的访问.
- 这种方法成功地应用于合成coniceine,一种性piperidine indolizidine的合成.
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