Very Simple One-Step Synthesis of Vinylphosphonates and Enamine Phosphonates by Direct Addition of Organolithium Reagents to 1-Alkynylphosphonates |
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| Authors: | Abdullatif Azab Dorit Moradov Abed Al-Aziz Al-Quntar Morris Srebnik |
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| Institution: | 1. Institute of Drug Research, School of Pharmacy , Hebrew University of Jerusalem , Jerusalem , 91120 , Israel;2. Institute of Drug Research, School of Pharmacy , Hebrew University of Jerusalem , Jerusalem , 91120 , Israel;3. Department of Material Engineering, Faculty of Engineering , Al-Quds University , Jerusalem , Palestinian Authority |
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| Abstract: | Abstract Direct addition of organolithium to 1-alkynylphosphonates (1) afforded vinylphosphonates and enamine phosphonates (2) in good to excellent yields. The reaction was carried out in dry THF at low temperature and proved to be completely stereoselective (syn addition). Alkyl, aryl, and haloalkyl groups were attached to the alkynyl entity, so the resulting vinylphosphonates contained various functional groups. The stereochemistry of the products as well as mechanism of the reaction were determined based on 1H and 13C NMR. The synthesis of enamine phosphonates in the absence of complicated, highly expensive organometallic catalysis has not been previously reported. |
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| Keywords: | 1-Alkynylphosphonates vinylphosphonates direct addition organolithium reagents stereoselectivity enamines |
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