Synthesis of alpha-heteroarylpropanoic acid via asymmetric hydroformylation catalyzed by Rh(I)-(R,S)-BINAPHOS and the subsequent oxidation.
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.
Tanaka
Ryo
R
Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Tokyo, Japan.
Nakano
Koji
K
Nozaki
Kyoko
K
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D009942:Organometallic Compounds; D011422:Propionates; D014753:Vinyl Compounds; D012238:Rhodium