Room Temperature Highly Enantioselective Nickel-Catalyzed Hydrovinylation

Room Temperature Highly Enantioselective Nickel-Catalyzed Hydrovinylation
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DOI:
10.1002/adsc.200900559
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发表时间:
2009-12-01
影响因子:
5.4
通讯作者:
Leitner, Walter
Leitner, Walter
中科院分区:
化学2区
文献类型:
--
作者:
Lassauque, Nicolas;Francio, Giancarlo;Leitner, Walter

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在室温下,基于新的亚磷酰胺(11 bR)-N-[(S)-1-(萘-1-基)乙基]-N-[(S)-1-(萘-2基)乙基]二萘并[2,1 '-d:1',2 '-f] [1,3,2]二氧磷杂环庚烯-4-胺的镍催化剂在富电子和贫电子乙烯基芳烃的加氢乙烯基化中提供优异的3-芳基丁-1-烯选择性(93-99%),具有高对映选择性(90- 95%ee)和TOF(高达8300 h(-1))。在几分钟内,有用的手性结构单元和中间体可以使用这种实用的催化体系合成。
At room temperature, nickel catalysts based on the new phosphoramidite (11bR)-N-[(S)-1-(naphthalen-1-yl)ethyl]-N-[(S)-1-(naphthalen-2yl)ethyl]dinaphtho[2,1'-d:1',2'-f] [1,3,2]dioxaphosphepin-4-amine provide excellent selectivities for 3-arylbut-1-enes (93-99%) with high enantioselectivities (90-95% ee) and TOFs (up to 8300 h(-1)) in the hydrovinylation of electron-rich and electron-poor vinylarenes. Within a few minutes, useful chiral building blocks and intermediates can be synthesized using this practical catalytic system.