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Updated: Jun 3, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Radical-transfer hydroamination of olefins with N-aminated dihydropyridines
Chih-Ming Chou1, Joyram Guin, Christian Mück-Lichtenfeld
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
Abstract:
An efficient synthesis of N-phthalimidyl, benzamidyl, acetamidyl, carbamoyl, and ureayl derivatives of dihydropyridines and the application of these reagents as precursors for N-centered radicals are presented. These aminated dihydropyridines could be used in radical-transfer hydroamination reactions of various electron-rich as well as nonactivated olefins in the presence of thiols as polarity-reversal catalysts. These reactions worked without the aid of any transition metal. Steric and electronic effects exerted by the N-substituents of the N-centered radicals are discussed. In contrast to most metal-catalyzed processes, the radical hydroamination delivered the opposite regioisomer with excellent anti-Markovnikov selectivity. Hydroamination products were obtained as protected amines that are readily isolated.
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