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
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
9 January 2006
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), .
(doi:10.1016/j.tet.2005.09.081).
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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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
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Date deposited: 05 Feb 2013 11:00
Last modified: 14 Mar 2024 12:54
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Contributors
Author:
Benjamin List
Author:
Arno Doehring
Author:
Maria T. Hechavarria Fonseca
Author:
Andreas Job
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