Facile biocatalytic syntheses of optically active 4-hydroxycyclohex-2-enone and 4-benzylthiacyclopent-2-enone

Tetrahedron Asymmetry

Volumn 15, Issue 18, 2004, Pages 2807-2809

  Morgan, Ben S ^a   Hoenner, Dorothée ^a   Evans, Paul ^b   Roberts, Stanley M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; BENZYL DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BIOCATALYST; CANDIDA ANTARCTICA; CHEMICAL REACTION; ENANTIOMER; KINETICS; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 4644307690     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.07.042     Document Type: Article

References (24)

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21. Typical laboratory procedure for preparation of (±)-4- hydroxycyclopent-2-enone 11: A 3 L five-necked round bottomed flask, equipped with long air condenser, thermometer pocket and a bubbler, was charged with furfuryl alcohol (25 g, 0.255 mol), potassium dihydrogen orthophosphate (6.3 g, 0.022 mol) and distilled water (1.5 L). The reaction was purged with a slow stream of nitrogen along with paddle stirring. It was heated to 99°C for 48 h. The solution developed brown insoluble impurities during the reaction. It was cooled to room temperature and then washed twice with ethyl acetate. The aqueous layer was concentrated to almost dryness under reduced pressure. The residue was then thoroughly extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was distilled under high vacuum using a fractionating column. Enone 11 was obtained as a pale yellow coloured oil distilling at 95-100°C at 0.5 mmHg (10.0 g, 40% yield)
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24. The silyl compound 14 is available from StylaCats Ltd, Runcorn, U.K.