Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates-Reference-Cited by-同舟云学术

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

Published:2020-09-24 Issue:03 Volume:53 Page:518-526
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Liu Teng¹,Huang Chao²,Cheng Feixiang¹,He Chixian¹,Wang Fan¹,Shen Xiang¹,Li Yongqin¹,Lang Man¹,Li Guijun¹

Affiliation:

1. Center for Yunnan-Guizhou Plateau Chemical Functional Materials and Pollution Control, College of Chemistry and Environmental Science, Qujing Normal University

2. School of Chemistry and Environment, Yunnan Minzu University

Abstract

AbstractA new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E-selectivity.

Funder

Applied Basic Research Foundation of Yunnan Province

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707292.pdf

Reference8 articles.

1. Recent Progress on Quinone Imine Ketals: Synthesis and Applications

2. Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone