Stereoselective synthesis of hex-2-(E)-en-4-yn-1,6-dioates and E,Z-muconic acid diesters via organo-catalyzed self-coupling of propiolates |
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Authors: | P Veeraraghavan Ramachandran Michael T Rudd M Venkat Ram Reddy |
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Institution: | Department of Chemistry, 560 Oval Drive, Purdue University, West Lafayette, IN 47907-2084, USA |
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Abstract: | Alkyl propiolate couples with itself in the presence of catalytic DABCO under very mild conditions to provide a quantitative yield of E-hex-2-en-4-yne dioates. Hydrogenation of these enyne dioates using Lindlar catalyst provides the corresponding E,Z-diene dioate, a common structural motif found in an array of natural products. |
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Keywords: | Enynes E Z-Dienes Muconic acid esters Self-coupling DABCO |
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