Enzymatic resolution of diethyl (3-hydroxy-1-butenyl) phosphonate

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8547-8549

  Attolini, Mireille ^a   Iacazio, Gilles ^a   Peiffer, Gilbert ^a   Maffei, Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Diethyl (3 hydroxy 1 butenyl) phosphonate; Enzymatic esterification; Resolution of organophosphorus compounds

Indexed keywords

DIETHYL (3 ACETOXY 1 BUTENYL)PHOSPHONATE; DIETHYL (3 HYDROXY 1 BUTENYL)PHOSPHONATE; ENZYME; LACTIC ACID ETHYL ESTER; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; ENZYME ACTIVITY; ESTERIFICATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0037131746     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02067-1     Document Type: Article

References (17)

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13. General procedure: The enzyme (50 mg) was added to a solution of 1 (48 mg; 0.23 mmol) and vinyl acetate (1 ml) in diisopropyl ether (10 ml), and the suspension was stirred at 30°C. The reaction was monitored by GC. After ca. 50% conversion (see Table 1 ), the mixture was filtered to remove the enzyme, the solvents were removed in vacuo, and the crude was subjected to flash chromatography (silica, ethyl acetate/methanol, 95:5) to yield 2 followed by 1. Ee's were measured by GC on a chiral column (CP-chirasil-DEX CB, 25 m, 32 mm I.D.), isothermal 160°C. Retention times: rac. 1: 12.9 min, (S)-2: 10.93 min, (R)-2: 11.38 min. Ee's for 1 were measured after acetylation.
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17. 2).