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

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Lee,  Ji-Woong
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

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.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-F498-5
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.