doi: 10.1021/jo0712190.
Epub 2007 Oct 10.
Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation
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- PMID: 17927247
- DOI: 10.1021/jo0712190
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Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation
J Org Chem.
.
Abstract
The asymmetric hydroformylation of vinyl heteroarenes (vinylfurans and vinylthiophenes) was investigated by using Rh(I)-BINAPHOS derivatives as a catalyst. The hydroformylation of vinylthiophenes 1 gave the corresponding branched aldehydes 2 with high enantiopurities as major products. Oxidation of the aldehydes 2 successfully afforded alpha-heteroarylpropanoic acids 4 in good yields. In addition, the aldehydes 2 were reduced to alcohols 5 without loss of enantiomeric excess.
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