手性双环胍催化的氧化吲哚和苯并呋喃-2(3H)-酮的对映选择性亚磺酰化反应
Chiral Bicyclic Guanidine-Catalyzed Enantioselective Sulfenylation of Oxindoles and Benzofuran-2(3H)-ones.
作者信息
Huang Lisha, Li Jiangtao, Zhao Yan, Ye Xinyi, Liu Yang, Yan Lin, Tan Choon-Hong, Liu Hongjun, Jiang Zhiyong
机构信息
Institute of Chemical Biology, Henan University , Kaifeng, Henan, 475004, P. R. China.
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University , Kaifeng, Henan, 475004, P. R. China.
出版信息
J Org Chem. 2015 Sep 4;80(17):8933-41. doi: 10.1021/acs.joc.5b01606. Epub 2015 Aug 12.
A chiral bicyclic guanidine-catalyzed enantioselective sulfenylation of 3-substituted oxindoles to N-(sulfanyl)succinimides has been developed. A series of unprecedented 3-sulfenylated oxindoles, such as 3-benzyl/alkyl-substituted 3-benzyl/alkyloxindoles, were obtained with high enantioselectivities (up to 98% ee). This methodology is also effective for the first asymmetric sulfenylation of benzofuran-2(3H)-ones, providing 3-benzyl-3-benzylthio-substituted benzofuran-2(3H)-ones with satisfactory results (up to 95% ee).
已开发出一种手性双环胍催化的3-取代氧化吲哚与N-（硫烷基）琥珀酰亚胺的对映选择性亚磺酰化反应。一系列前所未有的3-亚磺酰化氧化吲哚，如3-苄基/烷基取代的3-苄基/烷基氧化吲哚，以高对映选择性（高达98%ee）获得。该方法对于苯并呋喃-2(3H)-酮的首次不对称亚磺酰化反应也有效，能提供3-苄基-3-苄硫基取代的苯并呋喃-2(3H)-酮，结果令人满意（高达95%ee）。
Zotero 插件