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Synfacts 2008(2): 0170-0170  
DOI: 10.1055/s-2007-992441
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Hydroformylation of Vinylheteroarenes and Subsequent Oxidation

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
R. Tanaka, K. Nakano, K. Nozaki*
The University of Tokyo, Japan
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Publikationsdatum:
23. Januar 2008 (online)

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Significance

Notwithstanding Stille’s Pt(II)-BPPM/SnCl2 system (Organometallics 1991, 10, 1183), few reports exist for asymmetric hydroformylation of vinylheteroarenes. The present paper describes a Rh-BINAPHOS catalyst which gives hydroformylation products of namely vinylfurans and vinylthiophenes in good yields and moderate to excellent enantiomeric excesses. Furthermore, the convenient and highly practical oxidation protocol of the resulting aldehydes utilizing NaOClO offers access to corresponding chiral propanoic acids.