Efficient Access to cis-Hydrobenzo[b]oxepines: Rhodium(I)-Catalyzed Cyclization of Cyclohexadienone-Tethered o-Tolyl-Substituted Alkynes-Reference-Cited by-同舟云学术

Efficient Access to cis-Hydrobenzo[b]oxepines: Rhodium(I)-Catalyzed Cyclization of Cyclohexadienone-Tethered o-Tolyl-Substituted Alkynes

Published:2018-03-14 Issue:09 Volume:29 Page:1223-1228
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Wang Jia-Xin¹,Tan Yun-Xuan²,Liao Wei-Wei¹,Tian Ping²³^ORCID,Lin Guo-Qiang²³,Zhao Qian⁴

Affiliation:

1. College of Chemistry, Jilin University

2. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

3. Innovation Research Institute of Traditional Chinese Medicine (IRI), Shanghai University of Traditional Chinese Medicine

4. Jiangsu Key Laboratory of Chiral Drug Development, Jiangsu Aosaikang Pharmaceutical Co., Ltd.

Abstract

An efficient access to cis-hydrobenzo[b]oxepine frameworks has been established through rhodium(I)-catalyzed cyclization of cyclohexadienone-tethered o-tolyl-substituted alkynes (1,6-enynes). The cascade process involves regioselective α-arylrhodation of the alkyne, 1,4-rhodium migration, and conjugate addition to cyclohexadienone.

Funder

NSFC

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1591956.pdf

Cited by 14 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Recent Advances in Cyclization Reactions of 1,6‐Enynes;Advanced Synthesis & Catalysis;2024-02-02

2. Redox-neutral ipso/ortho alkenylcyanation of (hetero)arylboronic acid enabled by 1,4-rhodium migration and fragmentation;Science China Chemistry;2023-07-26

3. Exciting progress in the transition metal‐catalyzed synthesis of oxepines, benzoxepines, dibenzoxepines, and other derivatives;Applied Organometallic Chemistry;2021-12-28

4. Synthesis of Indole-Fused Oxepines via C–H Activation Initiated Diastereoselective [5 + 2] Annulation of Indoles with 1,6-Enynes;Organic Letters;2021-10-15

5. Transition-Metal-Catalyzed Functionalization of Alkynes with Organoboron Reagents: New Trends, Mechanistic Insights, and Applications;ACS Catalysis;2021-06-09