Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction

Wu, Song; Zhu, Xing‐Li; He, Wei; Wang, Rongming; Xie, Xiaohua; Qin, Da‐Bin; Jing, Lin‐Hai; Chen, Zeqin

doi:10.1016/j.tet.2013.11.016

Cited by 16 publications

(2 citation statements)

References 93 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, a recent report by Jing and co-workers highlighted that an example substrate previously assigned as an E-acylidene oxindole, was in fact the Z-isomer, moreover, the olefin geometry was found to have a significant impact on stereocontrol in Michael spirocyclisation reactions. 7 In connection with our own interests in the chemistry of 3-acylidene 2-oxindoles, we therefore set out to address this issue by establishing a routine and consistent method for the assignment of alkene stereochemistry in this class of compounds and report herein our findings.…”

Section: Introductionmentioning

confidence: 99%

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

et al. 2014

View full text Add to dashboard Cite

The designation of E/Z-geometrical isomers in 3-acylidene 2-oxindoles by NMR spectroscopy can lead to erroneous assignment of alkene stereochemistry because of the narrow chemical shift range observed over a large series of analogues. In contrast, UV-Vis spectroscopy offers a convenient and more reliable method for alkene stereochemical assignment. A combination of X-ray crystallography and theoretical studies shows that the observed differences in UV-Vis spectroscopic behaviour relate to the twisted conformation of the Z-isomers that provides reduced conjugation and weaker hypsochromic (blue-shifted) absorbances relative to those of the E-isomers.

show abstract

Section: Introductionmentioning

confidence: 99%

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

et al. 2014

View full text Add to dashboard Cite

show abstract

“…It was demonstrated that, under metal‐based catalysis or organocatalysis, 3‐isothiocyanato oxindoles were able to undergo [3+2] cycloadditions with differently functionalized olefins to deliver spirooxindoles enantioselectively (e.g., Scheme , 1b) . In addition, diastereoselective [3+2] cycloadditions between structurally different 3‐isothiocyanato oxindoles and olefins were also envisioned for the diastereoselective synthesis of spirooxindoles . Moreover, the use of imines (e.g., Scheme , 1c), ketones, aldehydes, alkynes, allenes, and azo compounds (Scheme , 1d) in [3+2] cycloadditions with 3‐isothiocyanato oxindoles for the diastereoselective and enantioselective preparation of spirooxindoles was reported.…”

Section: Introductionmentioning

confidence: 99%

[3+2] Cycloaddition between 3‐Isothiocyanato Oxindoles and Nitroso Compounds

et al. 2017

View full text Add to dashboard Cite

show abstract

Squaramide‐Catalyzed Enantioselective Cascade Approach to Bispirooxindoles with Multiple Stereocenters

Zhao

2016

Adv Synth Catal

View full text Add to dashboard Cite

A bifunctional squaramide‐catalyzed Michael/Michael cascade reaction for the construction of spirotetrahydrofuran bispirooxindoles was developed. The products were obtained in moderate to excellent yields with excellent diastereo‐ and enantioselectivities (up to >20:1 dr, >99% ee). This straightforward process serves as a powerful method for the enantioselective construction of potentially bioactive bispirooxindoles in which two of the four contiguous chiral centers are spiro all‐carbon quaternary centers on a single tetrahydrofuran ring. Meanwhile, the synthetic practicality of this methodology was illustrated by performing the reaction on a gram‐scale with the same efficiency and stereoselectivity.magnified image

show abstract

Highly efficient and diastereoselective construction of bispirooxindoles through a cascade Michael-cyclization reaction

Cited by 16 publications

References 93 publications

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

Studies on the stereochemical assignment of 3-acylidene 2-oxindoles

[3+2] Cycloaddition between 3‐Isothiocyanato Oxindoles and Nitroso Compounds

Squaramide‐Catalyzed Enantioselective Cascade Approach to Bispirooxindoles with Multiple Stereocenters

Contact Info

Product

Resources

About