One-pot three-component reaction of p-quinone monoacetals, l-proline and naphthols to afford N-aryl-2-arylpyrrolidines-Reference-Cited by-同舟云学术

One-pot three-component reaction of p-quinone monoacetals, l-proline and naphthols to afford N-aryl-2-arylpyrrolidines

Published:2021 Issue:2 Volume:8 Page:297-303
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Wang Xin¹²³⁴⁵,Li Gang¹²³⁴⁵,Li Xiaojie¹²³⁴⁵,Zhu Dunru¹²³⁴⁵^ORCID,Shen Ruwei¹²³⁴⁵^ORCID

Affiliation:

1. State Key Laboratory of Materials-Oriented Chemical Engineering

2. College of Chemistry and Chemical Engineering

3. Nanjing Tech University

4. Nanjing 210009

5. China

Abstract

A one-pot three-component reaction of p-quinone monoacetals (or p-quinol ethers), l-proline and naphthols is developed for the synthesis of N-aryl-2-arylpyrrolidines under mild conditions with high chemo- and regioselectivity.

Funder

Natural Science Foundation of Jiangsu Province

National Natural Science Foundation of China

Nanjing Tech University

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/QO/D0QO01294G

Reference56 articles.

1. E. R. Price and S. C.Johnson , Quinones: Occurrence, medicinal uses and physiological importance , NOVA Science , New York , 2013

2. Controlled-Coupling of Quinone Monoacetals by New Activation Methods: Regioselective Synthesis of Phenol-Derived Compounds

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

4. R. M. Moriarty and O.Prakash , Oxidation of Phenolic Compounds with Organohypervalent Iodine Reagents , Wiley-VCH , Weinheim, Germany , 2001 , pp 327–415

5. A Direct Route to Fluostatin C by a Fascinating Diels−Alder Reaction

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