Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles

被引:54
作者
Zhou, Xuan [1 ,2 ]
Dong, Guangbin [1 ,2 ]
机构
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA
[2] Univ Chicago, Dept Chem, 5735 S Ellis Ave, Chicago, IL 60637 USA
关键词
allenes; C-C activation; cycloaddition; nickel; small ring systems; C-C BOND; CARBON-CARBON BONDS; CLEAVAGE REACTIONS; RING-SYSTEMS; ACTIVATION; CARBOACYLATION; COMPLEXES; INSERTION; OLEFINS; BENZOCYCLOBUTENONES;
D O I
10.1002/anie.201609489
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein an intramolecular nickel-catalyzed (4+2) coupling between cyclobutanones and allenes, by C-C cleavage, is reported. The reaction provides a distinct approach for accessing [3.2.2] bicyclic scaffolds which are challenging to prepare through conventional approaches. The reaction is efficient, chemoselective, and pH/redox neutral. Room temperature conditions and low catalyst loadings can be adopted. Excellent enantioselectivity is also achieved.
引用
收藏
页码:15091 / 15095
页数:5
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