Base-catalyzed stereoselective intermolecular addition of imidazoles onto alkynes: an easy access to imidazolyl enamines |
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Authors: | Monika Patel Rakesh K SaunthawalAkhilesh K Verma |
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Institution: | Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi 110007, India |
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Abstract: | An efficient transition metal-free approach for the regio- and stereoselective addition of imidazoles 1a–f onto alkynes 2a–l to provide the Z- and E isomers of imidazolyl enamines 3a–q and 4a–d using catalytic amount of KOH is described. Stereoselectivity of the addition products (Z and E isomer) was found to be dependent upon time. Competitive experiments show that imidazole is less reactive than pyrrole and more reactive than aniline towards hydroamination. |
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Keywords: | Hydroamination Alkyne Enamines Imidazole Stereoselective N-Heterocycles |
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