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Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines

文献类型: 外文期刊

作者: Gao, Xing 1 ; Zhu, Dongyu 1 ; Jiang, Feng 1 ; Liao, Jianning 1 ; Wang, Wei 3 ; Wu, Yongjun 3 ; Zheng, Lufei 4 ; Guo, Hong 1 ;

作者机构: 1.China Agr Univ, Dept Chem, Beijing 100193, Peoples R China

2.China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China

3.Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China

4.Chinese Acad Agr Sci, Inst Qual Stand & Testing Technol Agroprod, Beijing 100081, Peoples R China

5.China Agr Univ, Dept Nutr & Hlth, Beijing 100193, Peoples R China

期刊名称:ORGANIC & BIOMOLECULAR CHEMISTRY ( 影响因子:3.412; 五年影响因子:3.134 )

ISSN: 1477-0520

年卷期:

页码:

收录情况: SCI

摘要: A diastereoselective (3 + 2) cycloaddition of N-sulfonyl ketimines with vinylethylene carbonates (VECs) in the presence of Pd(2)dba(3)center dot CHCl3 and PPh3 has been developed. The reaction of various substituted VECs and diverse cyclic N-sulfonyl ketimines proceeded smoothly under mild conditions, giving highly functionalized oxazolidine frameworks in good to excellent yields with moderate to good diastereoselectivities. With the use of spiroketal-based diphosphine SKP as a chiral ligand, an asymmetric version of the current (3 + 2) cycloaddition was achieved, and chiral products were obtained in >99% ee in most cases.

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