Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines
Hui-Jun Zhang1, Qing Gu2, Shu-Li You1,2
1School of Chemistry and Molecular Engineering , East China University of Science and Technology , 130 Meilong Road , Shanghai 200237 , China.
Abstract:
An efficient synthesis of pyrrolidinoindolines and tetrahydrofuranoindolines was achieved via Ni-catalyzed allylic dearomatization reactions of tryptophols and tryptamines. In the presence of 13 mol % of Ni(cod)2 and 10 mol % DPEphos, both tryptophols and tryptamines could react with aryl vinyl carbinols smoothly under mild conditions, affording 3-cinnamyl indolines in moderate to good yields with high chemo- and regioselectivity. This method features a broad substrate scope, a commercially available and inexpensive catalytic system, and readily available substrates.
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Cycloaddition Reactions: MO Requirements for Thermal Activation
Nucleophilic Aromatic Substitution: Elimination–Addition
Aldol Condensation with β-Diesters: Knoevenagel Condensation

![Radiosynthesis of 1-2-[18F]Fluoroethyl-L-Tryptophan using a One-pot, Two-step Protocol](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F63025.jpg&w=3840&q=50)
