Asymmetric cycloisomerization/[3 + 2] cycloaddition for the synthesis of chiral spiroisobenzofuran-1,3′-pyrrolidine derivatives
Literature Information
Publication Date
2021-10-08
DOI
10.1039/D1QO01194D
Impact Factor
5.281
Authors
Pei Dong, Long Chen, Zhendong Yang, Shunxi Dong, Xiaoming Feng
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
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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
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Molecular Formula:
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