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

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

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 Creators:
List, Benjamin1, Author           
Doehring, Arno1, Author           
Hechavarria Fonseca, Maria T.1, Author           
Job, Andreas2, Author
Rios Torres, Ramon1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, ou_1445585              
2Lanxess Deutschland GmbH, Building Q-18, 51369 Leverkusen Germany, ou_persistent22              

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 Abstract: We describe a highly efficient new methodology for the synthesis of (E)-α,β-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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Language(s): eng - English
 Dates: 2005-07-072005-10-202006-01-09
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1016/j.tet.2005.09.081
 Degree: -

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Title: Tetrahedron
  Other : Tetrahedron : the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry
Source Genre: Journal
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Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 62 (2-3) Sequence Number: - Start / End Page: 476 - 482 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020