手性布朗斯特酸催化2-甲氧基呋喃与脂肪族酮亚胺的对映选择性傅克反应生成。
Chiral Brønsted acid-catalyzed enantioselective Friedel-Crafts reaction of 2-methoxyfuran with aliphatic ketimines generated .
作者信息
Kondoh Azusa, Ota Yusuke, Komuro Takazumi, Egawa Fuyuki, Kanomata Kyohei, Terada Masahiro
机构信息
Research and Analytical Center for Giant Molecules , Graduate School of Science , Tohoku University , Aoba-ku , Sendai 980-8578 , Japan . Email:
Department of Chemistry , Graduate School of Science , Tohoku University , Aoba-ku , Sendai 980-8578 , Japan.
出版信息
Chem Sci. 2016 Feb 1;7(2):1057-1062. doi: 10.1039/c5sc03175c. Epub 2015 Oct 30.
An enantioselective Friedel-Crafts reaction with aliphatic ketimines generated from hemiaminal ethers catalyzed by a chiral Brønsted acid was investigated. The reaction of 2-methoxyfuran with (thio)hydantoin-derived hemiaminal methyl ether proceeded under the influence of a chiral phosphoric acid catalyst to afford the corresponding adduct possessing a quaternary stereogenic center in high yield with high enantioselectivity. Theoretical studies were also conducted to clarify the mechanism of the stereochemical outcome and the major factors contributing to the efficient enantioselection.
研究了在手性布朗斯特酸催化下，由半胺基醚生成的脂肪族酮亚胺的对映选择性傅克反应。在2-甲氧基呋喃与（硫）乙内酰脲衍生的半胺基甲醚的反应中，在手性磷酸催化剂的作用下，反应顺利进行，以高收率和高对映选择性得到了具有季碳立体中心的相应加合物。还进行了理论研究，以阐明立体化学结果的机理以及对有效对映选择性起主要作用的因素。
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