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

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

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...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-11, Vol.52 (46), p.12143-12147
Hauptverfasser: Bae, Han Yong, Sim, Jae Hun, Lee, Ji-Woong, List, Benjamin, Song, Choong Eui
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
aldol reaction
Antidepressants
Optical activity
organocatalysis
reaction mechanisms
Reproduction
synthetic methods
Thioesters
Utilities
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container_end_page 12147
container_issue 46
container_start_page 12143
container_title Angewandte Chemie International Edition
container_volume 52
creator Bae, Han Yong
Sim, Jae Hun
Lee, Ji-Woong
List, Benjamin
Song, Choong Eui
description 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.
doi_str_mv 10.1002/anie.201306297
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source Wiley Online Library Journals Frontfile Complete
subjects Aldehydes
aldol reaction
Antidepressants
Optical activity
organocatalysis
reaction mechanisms
Reproduction
synthetic methods
Thioesters
Utilities
title Organocatalytic Enantioselective Decarboxylative Aldol Reaction of Malonic Acid Half Thioesters with Aldehydes
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