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Synthesis 2018; 50(13): 2555-2566
DOI: 10.1055/s-0037-1609687
paper
© Georg Thieme Verlag Stuttgart · New York

A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride

Authors

  • Rui Ding

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Liyuan Lan

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Shuhui Li

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Yongguo Liu

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Shaoxiang Yang

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Hongyu Tian*

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

  • Baoguo Sun*

    Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, 100048 Beijing, P. R. of China   Email: tianhy@btbu.edu.cn   Email: sunbg@btbu.edu.cn

Financial support from the National Key Research and Development Program (2016YFD0400801), Beijing Postdoctoral Research Foundation (2017-22-011), and the Importation and Development of High-Caliber Talents Project of Beijing Municipal Institutions (CIT&TCD20140306) is gratefully acknowledged.
Further Information

Publication History

Received: 28 February 2018

Accepted after revision: 22 March 2018

Publication Date:
24 April 2018 (online)

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Graphical Abstract

Abstract

A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl+.

Key words

chlorolactonization - alkenoic acids - diphenyl sulfoxide - oxalyl­ chloride - chlorodiphenylsulfonium salt

Supporting Information