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Unexpected Regioselectivity in the Synthesis of Pyranonaphthoquinone via the Diels-Alder Reaction
Cui, Yi1,2,3; Jiang, Hao4; Li, Zhengtao1,2,3; Wu, Na1,2,3; Yang, Zhen1,2,3; Quan, Junmin1,2,3
2009-10-15
Source PublicationORGANIC LETTERS
ISSN1523-7060
Volume11Issue:20Pages:4628-4631
AbstractThe unusual regioselectivity in the Diels-Alder reactions of pyranoquinone 1 with (4,4-dimethoxybuta-1,3-dien-2-yloxy)trimethylsilane 2 are explored by both computations and experiments. The regioselectivity is controlled by the electrostatic interaction of the lactone ring-oxygen and the vicinal quinone oxygen on the transition structure, which can be tuned by the terminal methyl group of the butadienes.
DOI10.1021/ol901902v
Indexed BySCI ; IC
Language英语
WOS IDWOS:000270461300037
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:7[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67058
Collection中国科学院化学研究所
Corresponding AuthorYang, Zhen
Affiliation1.Beijing Univ, Coll Chem, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
2.Peking Univ, Shenzhen Grad Sch, Lab Chem Genom, Shenzhen 518055, Peoples R China
3.Beijing Univ, Coll Chem, BNLMS, Beijing 100871, Peoples R China
4.Jinan Univ, Coll Pharm, Inst Tradit Chinese Med & Nat Prod, Guangzhou 510632, Guangdong, Peoples R China
Recommended Citation
GB/T 7714
Cui, Yi,Jiang, Hao,Li, Zhengtao,et al. Unexpected Regioselectivity in the Synthesis of Pyranonaphthoquinone via the Diels-Alder Reaction[J]. ORGANIC LETTERS,2009,11(20):4628-4631.
APA Cui, Yi,Jiang, Hao,Li, Zhengtao,Wu, Na,Yang, Zhen,&Quan, Junmin.(2009).Unexpected Regioselectivity in the Synthesis of Pyranonaphthoquinone via the Diels-Alder Reaction.ORGANIC LETTERS,11(20),4628-4631.
MLA Cui, Yi,et al."Unexpected Regioselectivity in the Synthesis of Pyranonaphthoquinone via the Diels-Alder Reaction".ORGANIC LETTERS 11.20(2009):4628-4631.
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