Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis

doi:10.1021/acscatal.9b04183

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	Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis
	Chen, Bin 2; Zhang, Yunxing 2; Wu, Rui 2; Fang, Dongmei 1; Chen, Xiaozhen 1; Wang, Simin 2; Zhao, Yuqiong 2; Hu, Ping 2; Zhao, Ke-Qing 2; Wang, Bi-Qin 2
刊名	ACS CATALYSIS
	2019
卷号	9 期号:12 页码:11788-11793
关键词	1,3-dienes 2,8-dioxabicyclo[3.2.1]octane modular synthesis sequential catalysis cyclization cascade
ISSN号	2155-5435
DOI	10.1021/acscatal.9b04183
产权排序	2
文献子类	Article
英文摘要	A modular synthesis of 2,8-dioxabicyclo[3.2.1]octane (2,8-DOBCO) ketals is realized by sequential catalysis. The key intermediates, epsilon-hydroxyl-beta,gamma-unsaturated ketones, are readily available by Ni-catalyzed three-component coupling of 1,3-dienes, aldehydes, and acylzirconocene reagents. These polyfunctionalized ketones can undergo a V-catalyzed cascade of epoxidation and ring rearrangement to provide access to 6-hydroxyl-2,8-DOBCOs. Mechanistic studies indicate that the V(V) species, generated under epoxidation conditions, promotes the ring rearrangement in a stereospecific manner. Meanwhile, the epsilon-hydroxyl-beta-gamma-unsaturated ketones are transformed into 6-amino-2,8-DOBCOs by a Cu-catalyzed cascade of aziridination and ring rearrangement. In the end, the one-pot approach toward 6-hydroxyl- or 6-amino-2,8-DOBCOs from 1,3-diene, aldehydes, and acylzirconocene reagents is more favorable.
学科主题	Physical Chemistry/chemical Physics
URL标识	查看原文
WOS关键词	3-COMPONENT CONNECTION REACTION ; ZEROVALENT NICKEL-COMPLEX ; FORMAL TOTAL-SYNTHESIS ; ZARAGOZIC ACID-C ; STEREOSELECTIVE-SYNTHESIS ; ACYLZIRCONOCENE CHLORIDE ; CARBONYL-COMPOUNDS ; ORGANOMETALLIC REAGENTS ; ASYMMETRIC CYCLIZATION ; TETHERED ALDEHYDE
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000502169900113
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/30535]
专题	公共实验与分析中心
通讯作者	Cao, Peng
作者单位	1.Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China 2.Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610068, Sichuan, Peoples R China;
推荐引用方式 GB/T 7714	Chen, Bin,Zhang, Yunxing,Wu, Rui,et al. Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis[J]. ACS CATALYSIS,2019,9(12):11788-11793.
APA	Chen, Bin.,Zhang, Yunxing.,Wu, Rui.,Fang, Dongmei.,Chen, Xiaozhen.,...&Cao, Peng.(2019).Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis.ACS CATALYSIS,9(12),11788-11793.
MLA	Chen, Bin,et al."Modular Synthesis of 2,8-Dioxabicyclo[3.2.1]octanes by Sequential Catalysis".ACS CATALYSIS 9.12(2019):11788-11793.