We report the ()-3,3'-I-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of 2'-hydroxychalcones with ,'-cyclic azomethine imines, providing the corresponding ,'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >99:1 diastereomeric ratio and >99% enantiomeric excess). This catalytic system exhibits advantages of mild reaction conditions, high efficiency, and broad substrate scopes.
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http://dx.doi.org/10.1021/acs.orglett.2c02597 | DOI Listing |
J Org Chem
August 2024
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2'-hydroxychalcones with -2,2,2-trifluoroethylisatin ketimines catalyzed by a ()-3,3'-I-BINOL-boron complex was developed. A broad range of 3,2'-pyrrolidinyl spirooxindole derivatives bearing a CF-substituted pyrrolidine moiety with four contiguous stereocenters was prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and excellent stereocontrol.
View Article and Find Full Text PDFMolecules
January 2023
Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge de Viterbo Ferreira 228, 4050-313 Porto, Portugal.
Stereoselective synthesis has been emerging as a resourceful tool because it enables the obtaining of compounds with biological interest and high enantiomeric purity. Flavonoids are natural products with several biological activities. Owing to their biological potential and aiming to achieve enantiomerically pure forms, several methodologies of stereoselective synthesis have been implemented.
View Article and Find Full Text PDFOrg Lett
September 2022
NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, People's Republic of China.
We report the ()-3,3'-I-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of 2'-hydroxychalcones with ,'-cyclic azomethine imines, providing the corresponding ,'-bicyclic pyrazolidine derivatives with three contiguous tertiary stereocenters in high yields with excellent diastereo- and enantioselectivities (up to >99:1 diastereomeric ratio and >99% enantiomeric excess). This catalytic system exhibits advantages of mild reaction conditions, high efficiency, and broad substrate scopes.
View Article and Find Full Text PDFOrg Lett
October 2020
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
()-2,15-Cl-DHTP-boron complex catalyst for the asymmetric Diels-Alder cycloaddition of 2'-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 /, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions.
View Article and Find Full Text PDFChemistry
December 2018
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
A 2-alkenoylpyridine-bound N,N'-dioxide-Tb complex has been found to absorb visible light to reach the excited state, leading to the direct visible-light-excited catalytic enantioselective [2+2] cycloaddition of 2-alkenoylpyridines to various alkenes in the absence of an additional photosensitizer. Diverse enantioenriched cyclobutanes were successfully obtained (yields up to 70 %, >19:1 d.r.
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