title: Unexpected regioselectivity in the synthesis of pyranonaphthoquinone via the Diels-Alder reaction.
abstract: The 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.
authors.affiliation: Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Cui
authors.forename: Hao
authors.initials: H
authors.lastname: Jiang
authors.forename: Zhengtao
authors.initials: Z
authors.lastname: Li
authors.forename: Na
authors.initials: N
authors.lastname: Wu
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
authors.forename: Junmin
authors.initials: J
authors.lastname: Quan
mesh_terms: D007783:Lactones / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D055672:Static Electricity; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007783:Lactones; D009285:Naphthoquinones; D011714:Pyrans; D010100:Oxygen