Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst
Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst
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DOI：
10.1039/c2cc35583c
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发表时间：
2012-01-01
影响因子：
4.9
通讯作者：
Carbery, David R.
中科院分区：
文献类型：
--
作者：
Crittall, Matthew R.;Fairhurst, Nathan W. G.;Carbery, David R.
报道了第二代[6]-螺烯型DMAP有机催化剂的合成。该合成依赖于高度非对映选择性的Rh催化的[2 + 2 + 2]三炔环异构化，使用现有的立构中心来控制形成螺旋的意义。总之，已经实现了具有后续官能化能力的螺旋DMAP的可扩展（> 1g）、无分辨率的进入。
The synthesis of a second-generation [6]-helicenoidal DMAP organocatalyst is reported. The synthesis is reliant upon a highly diastereoselective Rh-catalysed [2 + 2 + 2] triyne cycloisomerization, using an existing stereocentre to control the sense of forming helicity. Taken together, a scalable (> 1 g), resolution-free entry to a helical DMAP with the capacity for subsequent functionalization, has been achieved.