Enhancing regiocontrol in carboaluminations of terminal alkynes.: Application to the one-pot synthesis of coenzyme Q10
Enhancing regiocontrol in carboaluminations of terminal alkynes.: Application to the one-pot synthesis of coenzyme Q10
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DOI：
10.1021/ol701469e
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发表时间：
2007-09-13
期刊：
影响因子：
5.2
通讯作者：
Servesko, Jeff
中科院分区：
文献类型：
--
作者：
Lipshutz, Bruce H.;Butler, Tom;Servesko, Jeff
两个新的“一代”的方法的进展，根岸carboaluminization的末端炔的报告。使用简单、廉价的添加剂改变Me 3Al和CP 2 ZrCl 2之间形成的Al-Zr络合物，产生特别有效的试剂混合物，其导致在1-炔的碳铝化后区域化学的几乎完全控制。一个及时的应用辅酶010是突出。避免了来自随后偶联的区域异构体，否则其将非常难以分离。
Two new "generations" of methodological advances are reported for the Negishi carboalumination of terminal alkynes. Use of simple, inexpensive additives that alter the Al-Zr complex formed between Me3Al and CP2ZrCl2 give rise to an especially effective reagent mix that results in virtually complete control of regiochemistry upon carboalumination of 1-alkynes. One timely application to coenzyme 010 is highlighted. Regioisomers from subsequent coupling, which would otherwise be very difficult to separate, are avoided.