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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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201306297