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

P. Veeraraghavan Ramachandran, Michael T. Rudd, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2547-2549
Number of pages3
JournalTetrahedron Letters
Volume46
Issue number15
DOIs
StatePublished - Apr 11 2005

Keywords

  • DABCO
  • E,Z-Dienes
  • Enynes
  • Muconic acid esters
  • Self-coupling

Fingerprint

Dive into the research topics of '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'. Together they form a unique fingerprint.

Cite this