Formal [4+1] Cyclization of ortho- or para-Quinone Methides with 3-Chlorooxindoles: Synthesis of 3,2 '-Tetrahydrofuryl Spirooxindoles

doi:10.1002/ajoc.202100363

	Formal [4+1] Cyclization of ortho- or para-Quinone Methides with 3-Chlorooxindoles: Synthesis of 3,2 '-Tetrahydrofuryl Spirooxindoles
	Tian, Xiaochen 1,2; Zhang, Xiaoli 1,2; Hou, Xiaohan 1,2; Ren, Weiwu 1,2,3; Li, Xiaoyang 1,2; Zhao, Fei4 ; Tao, Houchao4 ; Wang, Yang 1,2,3
	2021-09
发表期刊	ASIAN JOURNAL OF ORGANIC CHEMISTRY (IF:2.8[JCR-2023],2.8[5-Year])
ISSN	2193-5807
EISSN	2193-5815
DOI	10.1002/ajoc.202100363
摘要	A base promoted formal [4+1] cycloaddition of ortho- and para-quinone methides with 3-chlorooxindoles is reported to afford various functionalized 3,2 '-tetrahydrofuryl spirooxindoles in high yields under mild conditions. An unexpected reversal in diastereoselectivity was observed from these two types of reactions. Computational studies have provided insight into the origin of diastereoselection, and different configurations of 1,4-addition and 1,6-addition at the oxindole carbanionic center are found to give rise to different diastereomers. The anti-tumor activity of these structurally unique spirooxindole derivatives is reported.
关键词	3-Chlorooxindole [4+1] Cyclization ortho-Quinone methides para-Quinone methides Spirooxindoles
收录类别	SCIE ; IC ; CCR
语种	英语
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000683254600001
出版者	WILEY-V C H VERLAG GMBH
原始文献类型	Article; Early Access
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/127928
专题	iHuman研究所_PI研究组_陶厚朝组
通讯作者	Wang, Yang
作者单位	1.Ocean Univ China, Mol Synth Ctr, Chinese Minist Educ, Sch Med & Pharm, 5 Yushan Rd, Qingdao 266003, Peoples R China; 2.Ocean Univ China, Key Lab Marine Drugs, Chinese Minist Educ, Sch Med & Pharm, 5 Yushan Rd, Qingdao 266003, Peoples R China; 3.Qingdao Natl Lab Marine Sci & Technol QNLM, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China; 4.ShanghaiTech Univ, iHuman Inst, Ren Bldg,393 Middle Huaxia Rd, Shanghai 201210, Peoples R China
推荐引用方式 GB/T 7714	Tian, Xiaochen,Zhang, Xiaoli,Hou, Xiaohan,et al. Formal [4+1] Cyclization of ortho- or para-Quinone Methides with 3-Chlorooxindoles: Synthesis of 3,2 '-Tetrahydrofuryl Spirooxindoles[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY,2021.
APA	Tian, Xiaochen.,Zhang, Xiaoli.,Hou, Xiaohan.,Ren, Weiwu.,Li, Xiaoyang.,...&Wang, Yang.(2021).Formal [4+1] Cyclization of ortho- or para-Quinone Methides with 3-Chlorooxindoles: Synthesis of 3,2 '-Tetrahydrofuryl Spirooxindoles.ASIAN JOURNAL OF ORGANIC CHEMISTRY.
MLA	Tian, Xiaochen,et al."Formal [4+1] Cyclization of ortho- or para-Quinone Methides with 3-Chlorooxindoles: Synthesis of 3,2 '-Tetrahydrofuryl Spirooxindoles".ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021).