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Synfacts 2010(10): 1145-1145
DOI: 10.1055/s-0030-1258693
DOI: 10.1055/s-0030-1258693
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Chiral Chalcogen Peptides as Ligands for Aryl Transfer to Aldehydes
R. S. Schwab, L. C. Soares, L. Dornelles, O. E. D. Rodrigues*, M. W. Paixão, M. Godoi, A. L. Braga*
Universidade Federal de Santa Maria, Universidade Federal de São Carlos and Universidade Federal de Santa Catarina, Florianópolis, Brazil
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
The application of boronic acids in the arylation of aldehydes via boron-zinc exchange represents a convenient approach towards diarylmethanols. The authors developed a new class of chiral chalcogen peptides as ligands for this transformation. A number of chiral diarylmethanols were prepared with high yields and moderate to high enantioselectivities (51-91% ee). A two-step synthesis of (S)-orphenadrine (anticholinergic and antihistaminic agent) was accomplished.