A Gold(I)‐Catalyzed Cyclization/Semipinacol Rearrangement Cascade of 1,6‐Enynes to Access Spiro[4.5]decanes and 7‐Azaspiro[4.5]decanes-Reference-Cited by-同舟云学术

A Gold(I)‐Catalyzed Cyclization/Semipinacol Rearrangement Cascade of 1,6‐Enynes to Access Spiro[4.5]decanes and 7‐Azaspiro[4.5]decanes

Published:2023-01-24 Issue:3 Volume:365 Page:312-317
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Jin Da‐Ping¹,Cao Shi‐Qi¹,Cheng Fu¹,Xue Ze‐Sen¹,Li Run‐Ze¹,Pu Yan‐Lin¹,Zhu Dao‐Yong¹²,Bao Wen¹,Xu Xue‐Tao³,Wang Shao‐Hua¹^ORCID

Affiliation:

1. School of Pharmacy & State Key Laboratory of Applied Organic Chemistry & Collaborative Innovation Center for Northwestern Chinese Medicine Lanzhou University 222 Tianshui South Road, Chengguan District Lanzhou 730000 People's Republic of China

2. Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy Sichuan University Chengdu 610041 People's Republic of China

3. School of Biotechnology and Health Science Wuyi University Jiangmen 529020 People's Republic of China

Abstract

AbstractAn Au(I)‐catalyzed cyclization/semipinacol rearrangement cascade of 1,6‐enynes has been developed for the construction of spiro[4.5]decanes and 7‐azaspiro[4.5]decanes. The use of JohnPhosAuCl/NaBARF as a catalyst afforded functionalizable spirocyclic products with good diastereoselectivities of 6.7:1 to >20:1 dr. A plausible reaction mechanism has also been proposed on the basis of previous literature and our experimental results.

magnified image

Funder

National Natural Science Foundation of China

Science and Technology Program of Gansu Province

Department of Education of Guangdong Province

Fundamental Research Funds for the Central Universities

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202201266