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

Practical synthesis of (E)-?,?-unsaturated esters from aldehydes
Practical synthesis of (E)-?,?-unsaturated esters from aldehydes
Based on a modification of the Doebner–Knoevenagel reaction, a practical and highly efficient synthesis of a,b-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.
atom economy, doebner–knoevenagel reaction, malonic acid half esters, (E)-stereoselectivity, a, b-unsaturated esters
1615-4150
1558-1560
List, Benjamin
586d8ab5-60f2-42fe-898d-dffdf06234ea
Doehring, Arno
12e9517f-a74d-49bd-a0ee-bb9feed2da4d
Fonseca, Maria T. Hechavarria
4f1cec23-1579-40eb-9334-a114f4bac356
Wobser, Kathrin
bc11fded-4f6b-4301-9168-24cbf5c48ab8
van Thienen, Hendrik
52143d13-3acd-43c5-9a03-9dfe5dac9a8a
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Galilea, Pedro Llamas
321bb132-1920-4b18-9936-86dc4ecbf01c
List, Benjamin
586d8ab5-60f2-42fe-898d-dffdf06234ea
Doehring, Arno
12e9517f-a74d-49bd-a0ee-bb9feed2da4d
Fonseca, Maria T. Hechavarria
4f1cec23-1579-40eb-9334-a114f4bac356
Wobser, Kathrin
bc11fded-4f6b-4301-9168-24cbf5c48ab8
van Thienen, Hendrik
52143d13-3acd-43c5-9a03-9dfe5dac9a8a
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Galilea, Pedro Llamas
321bb132-1920-4b18-9936-86dc4ecbf01c

List, Benjamin, Doehring, Arno, Fonseca, Maria T. Hechavarria, Wobser, Kathrin, van Thienen, Hendrik, Rios Torres, Ramon and Galilea, Pedro Llamas (2005) Practical synthesis of (E)-?,?-unsaturated esters from aldehydes. Advanced Synthesis & Catalysis, 347 (11-13), 1558-1560. (doi:10.1002/adsc.200505196).

Record type: Article

Abstract

Based on a modification of the Doebner–Knoevenagel reaction, a practical and highly efficient synthesis of a,b-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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More information

Published date: 2005
Keywords: atom economy, doebner–knoevenagel reaction, malonic acid half esters, (E)-stereoselectivity, a, b-unsaturated esters
Organisations: Chemistry

Identifiers

Local EPrints ID: 347997
URI: http://eprints.soton.ac.uk/id/eprint/347997
ISSN: 1615-4150
PURE UUID: c13b3783-298c-43d0-b387-fb20039fc055
ORCID for Ramon Rios Torres: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 05 Feb 2013 11:14
Last modified: 12 Nov 2019 01:39

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Contributors

Author: Benjamin List
Author: Arno Doehring
Author: Maria T. Hechavarria Fonseca
Author: Kathrin Wobser
Author: Hendrik van Thienen
Author: Pedro Llamas Galilea

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