Gold(I)-Initiated Cycloisomerization/Diels-Alder/Retro-Diels-Alder Cascade Strategy to Biaryls

Shengfei Jin; Yujie Niu; Chengjun Liu; Lifeng Zhu; Yangming Li; Shanshan Cui; Zhiling Xiong; Maosheng Cheng; Bin Lin; Yongxiang Liu

doi:10.1021/acs.joc.7b01561

Gold(I)-Initiated Cycloisomerization/Diels-Alder/Retro-Diels-Alder Cascade Strategy to Biaryls

J Org Chem. 2017 Sep 1;82(17):9066-9074. doi: 10.1021/acs.joc.7b01561. Epub 2017 Aug 16.

Authors

Shengfei Jin^{1

2}, Yujie Niu^{1

3

2}, Chengjun Liu^{1

3

2}, Lifeng Zhu^{1

3

2}, Yangming Li^{1

3

2}, Shanshan Cui^{1

2}, Zhiling Xiong^{1

2}, Maosheng Cheng^{1

2}, Bin Lin^{1

2}, Yongxiang Liu^{1

3

2}

Affiliations

¹ Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University , Shenyang 110016, P. R. China.
² Institute of Drug Research in Medicine Capital of China , Benxi 117000, P. R. China.
³ Wuya College of Innovation, Shenyang Pharmaceutical University , Shenyang 110016, P. R. China.

PMID: 28776369
DOI: 10.1021/acs.joc.7b01561

Abstract

A unique approach to biaryls was developed on the basis of propargyl vinyl ethers and dienophiles substrates via a gold(I)-initiated cycloisomerization/Diels-Alder/retro-Diels-Alder cascade reaction. The scope and mechanism of the reaction were investigated on the basis of a series of synthetic substrates, control experiments, and DFT calculations.