Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence-Reference-Cited by-同舟云学术

Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence

Published:2017 Issue:81 Volume:53 Page:11201-11204
ISSN:1359-7345
Container-title:Chem. Commun.
language:en
Short-container-title:Chem. Commun.

Author:

Zhu Yanshuo¹²³⁴,Zhou Jing⁵⁶⁷⁸⁴^ORCID,Jin Shaojing¹²³⁴,Dong Huahui¹²³⁴,Guo Jiaomei¹²³⁴,Bai Xuguan¹²³⁴,Wang Qilin¹²³⁴^ORCID,Bu Zhanwei¹²³⁴

Affiliation:

1. College of Chemistry and Chemical Engineering

2. Henan University

3. Kaifeng 475004

4. China

5. School of Pharmaceutical Science

6. Chongqing Research Center for Pharmaceutical Engineering

7. Chongqing Medical University University

8. Chongqing 400016

Abstract

A TfOH-catalyzed highly diastereoselective Michael addition/ketalization sequence of 3-hydroxyoxindoles and ortho-hydroxychalcones was developed, leading to biologically important bridged ketal spirooxindoles in moderate to excellent yields.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2017/CC/C7CC05813F

Reference56 articles.

1. Chemistry of spiroketals

2. Cyclohexadienone Ketals and Quinols: Four Building Blocks Potentially Useful for Enantioselective Synthesis

3. Chemical variation of natural product-like scaffolds: design and synthesis of spiroketal derivatives

4. Enantioselective synthesis of spiroacetals: the conquest of a long-sought goal in asymmetric catalysis

5. Nonanomeric Spiroketals in Natural Products: Structures, Sources, and Synthetic Strategies

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