Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
复制标题
色氨酸与靛红衍生亚胺的催化剂控制化学选择性和对映选择性反应
DOI：
10.1021/acscatal.7b02279
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发表时间：
2017-10-01
期刊：
影响因子：
12.9
通讯作者：
Shi, Feng
中科院分区：
文献类型：
--
作者：
Jiang, Fei;Zhao, Dan;Shi, Feng
报道了色酚与吲哚亚胺在催化剂控制下的化学选择性和对映体选择性反应。在手性磷酸催化下，发生了非对映选择性和对映体选择性的脱芳环反应，而在手性方酰胺-叔胺存在下，发生了对映选择性加成反应。这两个反应都得到了3-取代的3-氨基-氧吲哚，总收率高(高达99%)和良好的立体选择性(高达>；95：5DR，99：1Er)。
Catalyst-controlled chemoselective and enantioselective reactions of tryptophols with isatin-derived imines were demonstrated. Under catalysis with a chiral phosphoric acid, diastereoselective and enantioselective dearomative cyclization occurred, while, in the presence of a chiral squaramide-tertiary amine, enantioselective addition occurred. Both reactions afforded 3-substituted 3-amino-oxindoles in generally good yields (up to 99%) and excellent stereoselectivities (up to >95:5 dr, 99:1 er).