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

doi:10.1016/j.tetlet.2005.02.098

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

53 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 language	English (US)
Pages (from-to)	2547-2549
Number of pages	3
Journal	Tetrahedron Letters
Volume	46
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2005.02.098
State	Published - Apr 11 2005

Keywords

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

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10.1016/j.tetlet.2005.02.098

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@article{311b2afc5be84e25a08930a0f83959b7,

title = "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",

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.",

keywords = "DABCO, E,Z-Dienes, Enynes, Muconic acid esters, Self-coupling",

author = "Ramachandran, \{P. Veeraraghavan\} and Rudd, \{Michael T.\} and Reddy, \{M. Venkat Ram\}",

year = "2005",

month = apr,

day = "11",

doi = "10.1016/j.tetlet.2005.02.098",

language = "English (US)",

volume = "46",

pages = "2547--2549",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "15",

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TY - JOUR

T1 - 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

AU - Ramachandran, P. Veeraraghavan

AU - Rudd, Michael T.

AU - Reddy, M. Venkat Ram

PY - 2005/4/11

Y1 - 2005/4/11

N2 - 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.

AB - 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.

KW - DABCO

KW - E,Z-Dienes

KW - Enynes

KW - Muconic acid esters

KW - Self-coupling

UR - https://www.scopus.com/pages/publications/15244341085

UR - https://www.scopus.com/pages/publications/15244341085#tab=citedBy

U2 - 10.1016/j.tetlet.2005.02.098

DO - 10.1016/j.tetlet.2005.02.098

M3 - Article

AN - SCOPUS:15244341085

SN - 0040-4039

VL - 46

SP - 2547

EP - 2549

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

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

Abstract

Keywords

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