Enantiofacial selective reduction of 2-allyl-2-carboethoxy-cyclopentanone mediated by baker's yeast.
Enantioselective reduction of 2-allyl-2-carboethoxy-cyclopentanone (2) was accomplished in high enantiomeric excess (> 99%), using baker's yeast in the presence of CuO, to obtain the (+)-2-allyl-2-carboethoxy-cyclopentanol derivative (6). This methodology also provides an entry to corresponding beta-keto ester (-)-(2), representing an important strategy to prepare chiral functionalized 2-oxabicyclic[3.3.0]octane and 2-oxabicyclic[4.4.0]nonane derivatives, useful synthons to access new bioactive compounds.
Fraga
C A
CA
Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio), Faculdade de Farmácia, Universidade Federal do Rio de Janeiro, Brazil.
Barreiro
E J
EJ
D003517:Cyclopentanes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D010088:Oxidoreductases / Q000378:metabolism; D012441:Saccharomyces cerevisiae / Q000378:metabolism*; D013237:Stereoisomerism
C102848:2-allyl-2-carboethoxycyclopentanone; D003517:Cyclopentanes; D010088:Oxidoreductases