Organocatalytic Enantioselective Nucleophilic Addition of Indole Imine 5-Methides
Yuxuan Li1, Jing Huang1,2, Zhengyu Han3
1Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Abstract:
Despite the enormous developments in the asymmetric transformations of indole imine methides (IIMs), the remote asymmetric induction involving IIMs remains challenging due to the spatial interaction requirement between the substrate and catalyst. Herein we report the first catalytic asymmetric nucleophilic addition to indole imine 5-methide (5-IIM), the only topological isomer of IIMs whose asymmetric addition remains unknown. Despite the challenging remote stereocontrol, high efficiency and respectable enantioselectivity were achieved to provide access to a range of enantioenriched indole-containing triaryl alkanes.
More Related Videos
Related Concept Videos
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Conjugate Addition of Enolates: Michael Addition
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Nucleophilic Aromatic Substitution: Elimination–Addition


