Practical synthesis of (E)-α,β-unsaturated esters from aldehydes

Benjamin List; Arno Doehring; Maria T. Hechavarria Fonseca; Kathrin Wobser; Hendrik Van Thienen; Ramon Rios Torres; Pedro Llamas Galilea

doi:10.1002/adsc.200505196

Practical synthesis of (E)-α,β-unsaturated esters from aldehydes

Benjamin List
, Arno Doehring
, Maria T. Hechavarria Fonseca
, Kathrin Wobser
, Hendrik Van Thienen
, Ramon Rios Torres
, Pedro Llamas Galilea

Chemistry

Max-Planck-Institut für Kohlenforschung

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

48 Scopus citations

Abstract

Based on a modification of the Doebner-Knoevenagel reaction, a practical and highly efficient synthesis of β,β-unsaturated esters with excellent regio- and stereoselectivity was developed. The reactions are catalyzed by 4-dimethylaminopyridine in DMF at room temperature or below. Both aliphatic and aromatic aldehydes can readily be used in the process.

Original language	British English
Pages (from-to)	1558-1560
Number of pages	3
Journal	Advanced Synthesis and Catalysis
Volume	347
Issue number	11-13
DOIs	https://doi.org/10.1002/adsc.200505196
State	Published - Oct 2005

Keywords

α,β-unsaturated esters
(E)-stereoselectivity
Atom economy
Doebner-Knoevenagel reaction
Malonic acid half esters

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10.1002/adsc.200505196

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title = "Practical synthesis of (E)-α,β-unsaturated esters from aldehydes",

abstract = "Based on a modification of the Doebner-Knoevenagel reaction, a practical and highly efficient synthesis of β,β-unsaturated esters with excellent regio- and stereoselectivity was developed. The reactions are catalyzed by 4-dimethylaminopyridine in DMF at room temperature or below. Both aliphatic and aromatic aldehydes can readily be used in the process.",

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author = "Benjamin List and Arno Doehring and \{Hechavarria Fonseca\}, \{Maria T.\} and Kathrin Wobser and \{Van Thienen\}, Hendrik and Torres, \{Ramon Rios\} and Galilea, \{Pedro Llamas\}",

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T1 - Practical synthesis of (E)-α,β-unsaturated esters from aldehydes

AU - List, Benjamin

AU - Doehring, Arno

AU - Hechavarria Fonseca, Maria T.

AU - Wobser, Kathrin

AU - Van Thienen, Hendrik

AU - Torres, Ramon Rios

AU - Galilea, Pedro Llamas

PY - 2005/10

Y1 - 2005/10

N2 - Based on a modification of the Doebner-Knoevenagel reaction, a practical and highly efficient synthesis of β,β-unsaturated esters with excellent regio- and stereoselectivity was developed. The reactions are catalyzed by 4-dimethylaminopyridine in DMF at room temperature or below. Both aliphatic and aromatic aldehydes can readily be used in the process.

AB - Based on a modification of the Doebner-Knoevenagel reaction, a practical and highly efficient synthesis of β,β-unsaturated esters with excellent regio- and stereoselectivity was developed. The reactions are catalyzed by 4-dimethylaminopyridine in DMF at room temperature or below. Both aliphatic and aromatic aldehydes can readily be used in the process.

KW - α,β-unsaturated esters

KW - (E)-stereoselectivity

KW - Atom economy

KW - Doebner-Knoevenagel reaction

KW - Malonic acid half esters

UR - https://www.scopus.com/pages/publications/27544497003

U2 - 10.1002/adsc.200505196

DO - 10.1002/adsc.200505196

M3 - Article

AN - SCOPUS:27544497003

SN - 1615-4150

VL - 347

SP - 1558

EP - 1560

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-13

ER -

Practical synthesis of (E)-α,β-unsaturated esters from aldehydes

Abstract

Keywords

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