Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones

doi:10.6023/cjoc201812038

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1383-1395.DOI: 10.6023/cjoc201812038 Previous Articles Next Articles

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碳酸钠促进的羧酸对α,β-不饱和酮的Oxa-Michael加成合成酯

王兴予^a, 朱雪庆^b, 姜炜^a, 高亚茹^b

a 西北工业大学附属中学西安 710072;
b 西北大学化学与材料科学学院西安 710069

收稿日期:2018-12-20 修回日期:2019-01-25 发布日期:2019-02-19
通讯作者: 高亚茹 E-mail:gyaru@nwu.edu.cn
基金资助:
国家自然科学基金（No.21702162）、陕西省教育厅科学基金（No.17JK0788）资助项目.

Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones

Wang Xingyu^a, Zhu Xueqing^b, Jiang Wei^a, Gao Yaru^b

a Middle School Attached to Northwestern Polytechnical University, Xi'an 710072;
b Department of Chemistry & Materials Science, Northwest University, Xi'an 710069

Received:2018-12-20 Revised:2019-01-25 Published:2019-02-19
Contact: 10.6023/cjoc201812038 E-mail:gyaru@nwu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21702162), and the Scientific Research Program Funded by Shaanxi Provincial Education Department (No. 17JK0788).

1. Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones.PDF(5183KB)

Abstract

Ester bonds are found widely in various fine chemicals, medicines, pesticides and functional materials. Despite the apparent simplicity, the construction of ester bonds often constitutes the most challenge in the synthesis of complex molecular containing ester functionality. Oxa-Michael addition represents an important class of organic reactions in carbon-heteroatom bond formation. The use of alcohol donors in oxa-Michael additions is well known. However, the use of carboxylic acid as the donor in the reaction is difficult due to the low activity of acid and a more pronounced reversibility of the reaction. To date, there is no general oxa-Michael addition of acids to α,β-unsaturated ketones reported. Herein, an efficient sodium carbonate promoted oxa-Michael addition of acids to α,β-unsaturated ketones to synthesize esters is reported. With a broad substrate scope, a well-common catalyst and simple operation, the approach provides a facile, practicable, economical, and environmentally benign method for the synthesis of esters.

Key words: esters, oxa-Michael addition, acids, α,β-unsaturated ketones, sodium carbonate aqueous solution

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Wang Xingyu, Zhu Xueqing, Jiang Wei, Gao Yaru. Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones[J]. Chin. J. Org. Chem., 2019, 39(5): 1383-1395.

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碳酸钠促进的羧酸对α,β-不饱和酮的Oxa-Michael加成合成酯

Synthesis of Esters via Sodium Carbonate Promoted Oxa-Michael Addition of Acids to α,β-Unsaturated Ketones

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