Tetrahedron letters

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

PV Ramachandran, MT Rudd, MVR Reddy

Index: Ramachandran, P. Veeraraghavan; Rudd, Michael T.; Reddy, M. Venkat Ram Tetrahedron Letters, 2005 , vol. 46, # 15 p. 2547 - 2549

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Citation Number: 35

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.