Direct Transition‐Metal‐Free Enantioselective Hydroxylation: Expeditious Access to 3‐Functionalized 3‐Hydroxy‐2‐oxindoles-Reference-Cited by-同舟云学术

Direct Transition‐Metal‐Free Enantioselective Hydroxylation: Expeditious Access to 3‐Functionalized 3‐Hydroxy‐2‐oxindoles

Published:2024-02-29 Issue:11 Volume:27 Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Zhao Shouqin¹,Yang Wen¹,Lan Yunfei¹²,Zhao Yanteng¹,Xu Yi¹,Liu Wanqing¹,Wang Linlin¹,Zhou Xin¹,Yu Changyan¹,Guo Ting¹,Yuan Lujiang¹,Jia Qianfa³,Ren Qiao¹^ORCID

Affiliation:

1. Engineering Research Center of Coptis Development & Utilization Ministry of Education College of Pharmaceutical Science Southwest University Chongqing 400715 P. R. China

2. Department of Laboratory Management Xi'an Jiaotong University Xi An Shi Xi'an 710049 P.R. China

3. Chongqing Key Laboratory of Inorganic Special Functional Materials College of Chemistry and Chemical Engineering Yangtze Normal University Chongqing 408100 P. R. China

Abstract

AbstractInspired by the ubiquitous prevalence of 3‐hydroxyoxindoles in natural products and pharmaceuticals, we herein disclose a direct and practical transition‐metal‐free asymmetric hydroxylation using commercially available Davis enantiopure oxaziridines as efficient oxidants, expeditiously affording an array of medicinally active 3‐functionalized 3‐hydroxy‐2‐oxindoles bearing quaternary stereocenters. The protocol features cheap reactants, ease of operation, scalability, and good functional‐group tolerance and efficient formal synthesis of natural products.

Funder

Chongqing Research Program of Basic Research and Frontier Technology

National Natural Science Foundation of China

Publisher

Wiley

Reference64 articles.

2. 3-Substituted-3-hydroxy-2-oxindole, an Emerging New Scaffold for Drug Discovery with Potential Anti-Cancer and other Biological Activities

3. C. Marti E. M. Carreira Eur. J. Org. Chem.2003 2209–2219.

4. Enantioselective Total Synthesis of Convolutamydines B and E

5. Total Synthesis of Donaxaridine