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A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-?,?-unsaturated esters from aldehydes

A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-?,?-unsaturated esters from aldehydes
A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-?,?-unsaturated esters from aldehydes
We describe a highly efficient new methodology for the synthesis of (E)-?,?-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.
(E)-stereoselectivity, ?, ?-unsaturated esters, doebner–knoevenagel reaction, dmap-catalysis
0040-4020
476-482
List, Benjamin
586d8ab5-60f2-42fe-898d-dffdf06234ea
Doehring, Arno
12e9517f-a74d-49bd-a0ee-bb9feed2da4d
Hechavarria Fonseca, Maria T.
2a7817fc-b53a-419f-a36a-33f683301325
Job, Andreas
c8d7523e-03e7-4cca-b925-e27e835fd17a
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
List, Benjamin
586d8ab5-60f2-42fe-898d-dffdf06234ea
Doehring, Arno
12e9517f-a74d-49bd-a0ee-bb9feed2da4d
Hechavarria Fonseca, Maria T.
2a7817fc-b53a-419f-a36a-33f683301325
Job, Andreas
c8d7523e-03e7-4cca-b925-e27e835fd17a
Rios Torres, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441

List, Benjamin, Doehring, Arno, Hechavarria Fonseca, Maria T., Job, Andreas and Rios Torres, Ramon (2006) A Practical, efficient, and atom economic alternative to the Wittig and Horner–Wadsworth–Emmons reactions for the synthesis of (E)-?,?-unsaturated esters from aldehydes. Tetrahedron, 62 (2-3), 476-482. (doi:10.1016/j.tet.2005.09.081).

Record type: Article

Abstract

We describe a highly efficient new methodology for the synthesis of (E)-?,?-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.

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More information

Published date: 9 January 2006
Keywords: (E)-stereoselectivity, ?, ?-unsaturated esters, doebner–knoevenagel reaction, dmap-catalysis
Organisations: Chemistry

Identifiers

Local EPrints ID: 347994
URI: http://eprints.soton.ac.uk/id/eprint/347994
ISSN: 0040-4020
PURE UUID: 93977faf-cdf7-4722-9177-6b1fd57bf561
ORCID for Ramon Rios Torres: ORCID iD orcid.org/0000-0002-3843-8521

Catalogue record

Date deposited: 05 Feb 2013 11:00
Last modified: 26 Nov 2019 01:37

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