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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. 2007 Nov 09; 72(23):8671-6.JO

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.

Authors+Show Affiliations

Tanaka R
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Tokyo, Japan.
Nakano K
No affiliation info available
Nozaki K
No affiliation info available

MeSH

AldehydesCatalysisMolecular StructureOrganometallic CompoundsOxidation-ReductionPropionatesRhodiumStereoisomerismVinyl Compounds

Pub Type(s)

Journal Article

Language

eng

PubMed ID

17927247

Citation

Tanaka, Ryo, et al. "Synthesis of Alpha-heteroarylpropanoic Acid Via Asymmetric Hydroformylation Catalyzed By Rh(I)-(R,S)-BINAPHOS and the Subsequent Oxidation." The Journal of Organic Chemistry, vol. 72, no. 23, 2007, pp. 8671-6.
Tanaka R, Nakano K, Nozaki K. Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation. J Org Chem. 2007;72(23):8671-6.
Tanaka, R., Nakano, K., & Nozaki, K. (2007). Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation. The Journal of Organic Chemistry, 72(23), 8671-6.
Tanaka R, Nakano K, Nozaki K. Synthesis of Alpha-heteroarylpropanoic Acid Via Asymmetric Hydroformylation Catalyzed By Rh(I)-(R,S)-BINAPHOS and the Subsequent Oxidation. J Org Chem. 2007 Nov 9;72(23):8671-6. PubMed PMID: 17927247.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation. AU - Tanaka,Ryo, AU - Nakano,Koji, AU - Nozaki,Kyoko, Y1 - 2007/10/10/ PY - 2007/10/12/pubmed PY - 2008/1/8/medline PY - 2007/10/12/entrez SP - 8671 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 72 IS - 23 N2 - 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. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/17927247/Synthesis_of_alpha_heteroarylpropanoic_acid_via_asymmetric_hydroformylation_catalyzed_by_Rh_I___RS__BINAPHOS_and_the_subsequent_oxidation_ L2 - https://doi.org/10.1021/jo0712190 DB - PRIME DP - Unbound Medicine ER -