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  Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes

Bae, H. Y., Sim, J. H., Lee, J.-W., List, B., & Song, C. E. (2013). Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes. Angewandte Chemie International Edition, 52(46), 12143-12147. doi:10.1002/anie.201306297.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-F498-5 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-4C56-3
Genre: Journal Article

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 Creators:
Bae , Han Yong1, Author
Sim, Jae Hun1, Author
Lee, Ji-Woong2, Author           
List, Benjamin2, Author           
Song, Choong Eui1, Author
Affiliations:
1Department of Chemistry, Sungkyunkwan University, 300, Cheoncheon, Jangan, Suwon, 440‐746 (Korea), ou_persistent22              
2Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, ou_1445585              

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Free keywords: aldehydes; aldol reaction; organocatalysis; reaction mechanisms; synthetic methods
 Abstract: Copycat: A highly enantioselective biomimetic aldol reaction of malonic acid half thioesters with a variety of aldehydes affords optically active β‐hydroxy thioesters by employing the cinchona‐derived sulfonamide organocatalyst 1. The synthetic utility of this protocol was demonstrated by performing formal syntheses of the antidepressants (R)‐fluoxetine, (R)‐tomoxetine, (−)‐paroxetine, and (R)‐duloxetine.

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Language(s): eng - English
 Dates: 2013-07-192013-09-232013-11-11
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201306297
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 52 (46) Sequence Number: - Start / End Page: 12143 - 12147 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851