Dynamic Control of Chiral Space in a Catalytic Asymmetric Reaction Using a Molecular Motor
Dynamic Control of Chiral Space in a Catalytic Asymmetric Reaction Using a Molecular Motor
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DOI：
10.1126/science.1199844
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发表时间：
2011-03-18
期刊：
影响因子：
56.9
通讯作者：
Feringa, Ben L.
中科院分区：
文献类型：
--
作者：
Wang, Jiaobing;Feringa, Ben L.
酶和合成手性催化剂已被广泛应用于生产单一对映体，但原位切换催化体系的手性偏好是很难实现的。在这里，我们报告的光驱动的分子马达与集成的催化功能，其中在360度单向旋转周期期间的配置的逐步变化支配催化剂的性能，无论是相对于活性和绝对立体控制在不对称变换。在一个完整的旋转循环期间，形成催化剂，其提供共轭加成反应的手性产物的外消旋（R，S）或优选R或S对映异构体。这个催化系统演示了不同的分子任务如何以顺序的方式进行，顺序由旋转循环的方向性控制。
Enzymes and synthetic chiral catalysts have found widespread application to produce single enantiomers, but in situ switching of the chiral preference of a catalytic system is very difficult to achieve. Here, we report on a light-driven molecular motor with integrated catalytic functions in which the stepwise change in configuration during a 360 degrees unidirectional rotary cycle governs the catalyst performance both with respect to activity and absolute stereocontrol in an asymmetric transformation. During one full rotary cycle, catalysts are formed that provide either racemic (R,S) or preferentially the R or the S enantiomer of the chiral product of a conjugate addition reaction. This catalytic system demonstrates how different molecular tasks can be performed in a sequential manner, with the sequence controlled by the directionality of a rotary cycle.