Copper Catalyzed Asymmetric [4+2] Annulations of D-A Cyclobutanes with Aldehydes  被引量:5

Copper Catalyzed Asymmetric [4+2] Annulations of D-A Cyclobutanes with Aldehydes

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作  者:Jiang-Lin Hu Li Zhou Lijia Wang Zuowei Xie Yong Tang 

机构地区:[1]The State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China [2]Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road,Shanghai 200032, China [3]Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, China

出  处:《Chinese Journal of Chemistry》2018年第1期47-50,共4页中国化学(英文版)

基  金:We thank for the financial support from the National Natural Science Foundation of China (Nos. 21421091 and 21432011), the National Basic Research Program of China (973 Program) (2015CB856600), the Natural Science Foundation of Shanghai (17ZR1436900), the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000) and the Youth Innovation Promotion Association CAS (2017301). We thank Dr. Xue-Bing Leng for X-ray crystal analysis

摘  要:Copper catalyzed enantioselective [4+2] annulations of D-A cyclobutanes and aldehydes have been developed. In the presence of a side arm modified chiral bisoxazoline (SaBOX) ligand, the [4+2] annulations proceeded smoothly with a broad substrate scope. 22 examples were studied, leading to the corresponding products with various functional groups in 41%-99% yields with 〉99/1 dr and 90%-96% ee. The resulting product with two ester groups was mono-reduced, giving the corresponding product in excellent diastereoselectivity without loss of the enantiopurity.Copper catalyzed enantioselective [4+2] annulations of D-A cyclobutanes and aldehydes have been developed. In the presence of a side arm modified chiral bisoxazoline (SaBOX) ligand, the [4+2] annulations proceeded smoothly with a broad substrate scope. 22 examples were studied, leading to the corresponding products with various functional groups in 41%-99% yields with 〉99/1 dr and 90%-96% ee. The resulting product with two ester groups was mono-reduced, giving the corresponding product in excellent diastereoselectivity without loss of the enantiopurity.

关 键 词:[4+2] annulation CYCLOBUTANE enantioselective COPPER BISOXAZOLINE 

分 类 号:O624.11[理学—有机化学] TQ225.52[理学—化学]

 

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