Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines,ACS Catalysis

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Catalyst-Controlled Chemoselective and Enantioselective Reactions of Tryptophols with Isatin-Derived Imines
ACS Catalysis ( IF 11.3 ) Pub Date : 2017-09-19 00:00:00 , DOI: 10.1021/acscatal.7b02279
Fei Jiang ₁ , Dan Zhao ₂ , Xue Yang ₁ , Fu-Ru Yuan ₁ , Guang-Jian Mei ₁ , Feng Shi ₁

Affiliation

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).

中文翻译：

色酚与Isatin衍生的亚胺的催化剂控制的化学选择性和对映选择性反应

证明了胰蛋白酶与伊斯汀衍生的亚胺的催化剂控制的化学选择性和对映选择性反应。在手性磷酸的催化下，发生了非对映选择性和对映选择性脱芳香化环化反应，而在存在手性方酰胺-叔胺的情况下，发生了对映选择性加成反应。两种反应均以通常良好的产率（高达99％）和优异的立体选择性（高达＞ 95∶5 dr，99∶1 er）提供3-取代的3-氨基-吲哚。

更新日期：2017-09-20

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