Stereoselective Synthesis of (E)-β-Aryloxyl and Alkyloxyl Acrylates Through DABCO-Catalysed Michael Additions of Phenols and Alcohols to Ethyl 2,3-Butadienoate-Reference-Cited by-同舟云学术

Stereoselective Synthesis of (E)-β-Aryloxyl and Alkyloxyl Acrylates Through DABCO-Catalysed Michael Additions of Phenols and Alcohols to Ethyl 2,3-Butadienoate

Published:2016-06 Issue:6 Volume:40 Page:364-367
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Wei Feng¹,Haibo Wu¹,Houjun Qian¹,Zhengyi Li¹²,Xiaoqiang Sun¹²,Zhiming Wang¹²

Affiliation:

1. Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P.R. China

2. Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University, Changzhou, Jiangsu 213164, P.R. China

Abstract

The development of DABCO-catalysed Michael addition of phenols and alcohols to ethyl 2,3-butadienoate provides an efficient synthetic pathway to ( E)- β-aryloxyl and alkyloxyl acrylates in i-PrOH or under solvent-free conditions. The major advantages of the present method are wide substrate scope, mild reaction conditions, high stereoselectivity, and good reaction yields.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751916X14631336104179

Reference25 articles.

1. Synthesis of Pyrroles by Gold(I)-Catalyzed Amino−Claisen Rearrangement of N-Propargyl Enaminone Derivatives

2. Copper-Catalyzed, C–C Coupling-Based One-Pot Tandem Reactions for the Synthesis of Benzofurans Using o-Iodophenols, Acyl Chlorides, and Phosphorus Ylides

3. Ylide Hydrolysis in Tandem Reactions: A Highly Z/E-Selective Access to 3-Alkylidene Dihydrobenzofurans and Related Analogues

4. Palladium-Catalyzed Oxidative Cyclization of 3-Phenoxyacrylates: An Approach To Construct Substituted Benzofurans from Phenols

5. Phosphine/Palladium-Catalyzed Syntheses of Alkylidene Phthalans, 3-Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol

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