手性方酰胺催化合成芳香族[6,5]螺缩酮的不对称螺缩酮化反应
Chiral Squaramide Catalyzed Asymmetric Spiroketalization toward Aromatic [6,5] Spiroketals.
作者信息
Roy Tarun Kumar, Gorad Sachin S, Ghorai Prasanta
机构信息
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, India.
出版信息
Org Lett. 2022 Mar 18;24(10):1889-1894. doi: 10.1021/acs.orglett.2c00074. Epub 2022 Mar 3.
Herein is disclosed an efficient enantio- and diastereoselective spiroketalization of aromatic ketone tethered to -homoformyl and enone moiety via enol formation using quinine derived squaramide organocatalyst to access aromatic [6,5] spiroketals with complete atom economy. Furthermore, aromatic spiroketals undergo Brønsted acid catalyzed Piancatelli type rearrangement to provide dihydronaphtho[1,2-]furans with retention of the enantioselectivities.
本文公开了一种高效的对映选择性和非对映选择性螺缩酮化反应，该反应通过使用奎宁衍生的方酰胺有机催化剂形成烯醇，将与高甲酰基和烯酮部分相连的芳族酮进行螺缩酮化，以完全原子经济性获得芳族[6,5]螺缩酮。此外，芳族螺缩酮经布朗斯特酸催化的皮安卡特利型重排反应，可提供对映选择性得以保留的二氢萘并[1,2 -]呋喃。
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