Enantioselective Construction of Spiroindolines with Three Contiguous Stereogenic Centers and Chiral Tryptamine Derivatives via Reactive Spiroindolenine Intermediates

• Published in: Angewandte Chemie International Edition Vol. 54; no. 47; pp. 14146 - 14149
• Main Authors: Zhuo, Chun-Xiang, Zhou, Yong, Cheng, Qiang, Huang, Lin, You, Shu-Li
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 16.11.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: asymmetric catalysis; Chemistry; Chemistry, Multidisciplinary; dearomatization; heterocycles; iridium; Physical Sciences; Science & Technology; synthetic methods; ARYLATIVE DEAROMATIZATION; CARBON; COMMUNESIN F; ALKYLATION; dearomatization; QUATERNARY STEREOCENTERS; asymmetric catalysis; iridium; ASYMMETRIC ALLYLIC DEAROMATIZATION; heterocycles; ALPHA-ALLYLATION; INDOLE ALKALOIDS; synthetic methods; SPIRO
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201507193

The highly efficient synthesis of the enantioenriched spiroindolines by iridium‐catalyzed asymmetric allylic dearomatization and reduction is presented. Spiroindolines containing three contiguous stereogenic centers were obtained with excellent diastereo‐ and enantioselectivity. In addition, a chiral tryptamine derivative could be easily accessed in good yield with excellent ee value through an unprecedented dearomatization/retro‐Mannich/hydrolysis cascade reaction of an indole derivative. On a tryp: The highly efficient synthesis of enantioenriched spiroindolines by an iridium‐catalyzed asymmetric allylic dearomatization and reduction has been realized. The spiroindolines contain three contiguous chiral centers and are obtained with excellent diastereo‐ and enantioselectivities. Furthermore, a chiral tryptamine derivative could also be accessed with excellent enantioselectivity.