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Synfacts 2011(7): 0697-0697  
DOI: 10.1055/s-0030-1260478
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of (S)-Ketoprofen

Contributor(s): Philip Kocienski
A. E. Allen, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

A synthesis of the non-steroidal anti-inflammatory drug (S)-ketoprofen exemplifies a new general tandem catalysis approach to the enantioselective organocatalytic α-arylation of aldehydes. The scope of the reaction is illustrated by 22 examples (67-95% yield, 91-94% ee) involving ten different aldehydes and 13 different ­diaryliodonium salts. A five-step synthesis of ­catalyst C (17% overall) from l-phenylglycine N-methylamide is provided.