Pd-Catalyzed Dienylation of Propargylic Esters Enabling Highly Stereoselective Synthesis of Danishefsky-Type Trisubstituted Dienes
Chen Zhou
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorMengfu Dai
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorXiaoyu Yin
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorMingyue Zhang
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorWeijin Gu
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorCorresponding Author
Liang-An Chen
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
E-mail: [email protected]Search for more papers by this authorChen Zhou
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorMengfu Dai
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorXiaoyu Yin
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorMingyue Zhang
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorWeijin Gu
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
Search for more papers by this authorCorresponding Author
Liang-An Chen
Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Jiangsu Key Laboratory of New Power Batteries, School of Chemistry and Materials Science, Nanjing Normal University, Nanjing, Jiangsu, 210023 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
The stereochemical synthesis of highly substituted Danishefsky-type dienes remains unsolved in organic chemistry. We describe a simple and efficient approach for the stereoselective synthesis of Danishefsky-type trisubstituted dienes from readily available propargylic esters via Pd-catalyzed dienylation reaction through the key intermediate metallacyclobutene in a regio-, chemo- and stereoselective fashion. This method facilitates a broad range of challenging trisubstituted dienes with a high level of stereocontrol. The synthetic utilities of oxygenated trisubstituted dienes have been demonstrated by the downstream chemistry, which notably undergoes Diels-Alder reaction with a variety of electron-deficient dienophiles to furnish multisubstituted cyclohexenes in good yields with excellent stereoselectivity.
Supporting Information
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