α'-亚烷基-2-环己烯酮的交叉共轭三烯胺催化：在β,γ-区域选择性氮杂狄尔斯-阿尔德反应中的应用
Cross-conjugated Trienamine Catalysis with α'-Alkylidene 2-Cyclohexenones: Application in β,γ-Regioselective Aza-Diels-Alder Reaction.
作者信息
Zhou Zhi, Wang Zhou-Xiang, Ouyang Qin, Xiao Wei, Du Wei, Chen Ying-Chun
机构信息
Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
College of Pharmacy, Third Military Medical University, Chongqing, 400038, P. R. China.
出版信息
Chemistry. 2017 Feb 24;23(12):2945-2949. doi: 10.1002/chem.201605606. Epub 2017 Feb 1.
Endo-type cross-conjugated trienamines between highly congested α'-alkylidene 2-cyclohexenones and a chiral primary amine catalyst serve as HOMO-raised dienophiles in inverse-electron-demand aza-Diels-Alder cycloadditions with a number of 1-azadiene substrates. The reactions exhibit exclusive β,γ-regioselectivity, and multifunctional products with high molecular complexity are efficiently constructed in excellent diastereo- and enantioselectivity (>19:1 d.r., up to 99 % ee).
在高度拥挤的α'-亚烷基-2-环己烯酮与手性伯胺催化剂之间形成的内型交叉共轭三烯胺，在与多种1-氮杂二烯底物进行的反电子需求氮杂狄尔斯-阿尔德环加成反应中，作为HOMO升高的亲双烯体。这些反应表现出独特的β,γ区域选择性，并且能够以优异的非对映选择性和对映选择性（>19:1的非对映体比例，高达99%ee）高效构建具有高分子复杂性的多功能产物。
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