Asymmetric cycloisomerization/[3 + 2] cycloaddition for the synthesis of chiral spiroisobenzofuran-1,3′-pyrrolidine derivatives

文献情報

出版日 2021-10-08

DOI 10.1039/D1QO01194D

インパクトファクター 5.281

著者

Pei Dong, Long Chen, Zhendong Yang, Shunxi Dong, Xiaoming Feng

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要旨

An asymmetric catalytic tandem cycloisomerization/[3 + 2] cycloaddition was achieved by a combined system of Au(I) and a chiral N,N′-dioxide–Dy(III) complex. Various enantioenriched 3H-spiroisobenzofuran-1,3′-pyrrolidine derivatives from a number of 2,2′-diester aziridines and 2-ethynyl benzyl alcohols were afforded in moderate to good yields with high diastereo- and enantioselectivities (up to 81% yield, >19 : 1 dr, 95% ee). On the basis of control experiments and the absolute configuration of the product, possible working modes were proposed to understand the origin of chiral control.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Asymmetric cycloisomerization/[3 + 2] cycloaddition for the synthesis of chiral spiroisobenzofuran-1,3′-pyrrolidine derivatives

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