Chemo-enzymatic preparations of (R)- and (S)-3-iodocyclohex-2-en-1-yl acetate

Synthetic Communications

Volumn 33, Issue 14, 2003, Pages 2487-2496

  Barnier, J P ^a   Blanco, L ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 IODOCYCLOHEX 2 EN 1 YLACETATE; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; KINETICS; SEPARATION TECHNIQUE; SYNTHESIS; TRANSESTERIFICATION;

EID: 0042564674     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021839     Document Type: Article

References (13)

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2. The pallado-catalyzed preparation of optically active (3-hydroxy-cyclohex-1-enyl)phosphonate was reported from enantiomerically enriched 3-bromocyclohex-2-en-1-ol: Attolini, M.; Bouguir, F.; Iacazio, G.; Peiffer, G.; Maffei, M. Tetrahedron 2001, 57, 537-543.
3. Barnier, J.-P.; Morisson, V.; Volle, I.; Blanco, L. Tetrahedron: Asymmetry 1999, 10, 1107-1117.
4. 1H-NMR of the corresponding α-methoxy α-trifluoromethylphenylacetate and from its chiroptical properties.
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6. p)].
7. Carrea, G.; Danieli, B.; Palmisano, G.; Riva, S.; Santagostino, M. Tetrahedron: Asymmetry 1992, 3, 775-784.
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10. Novozym® was an immobilized form of lipase B from Candida antarctica prepared by Novo Nordisk A/S (Denmark). Now a similar immobilized-enzyme, named Chirazyme® L-2, c-f, C2 Lyo., is prepared by Boehringer Mannheim GmbH.
11. Enantiomeric excesses of optically active acetates 4-(S) and 4-(R) (prepared from alcohol 3-(R)) could be determined by gas chromatography on a chiral capillary column (Cydex B). With a 25m column (0.25mn id, gas carrier: helium, P = 70 KPa, 80°C) the retention times were around 2h but the separation of the enantiomers was not sufficient to obtain accurate measurements.
12. Lallemand, J.-Y.; Leclaire, M.; Levet, R.; Aranda, G. Tetrahedron: Asymmetry 1993, 4, 1775-1778.
13. Mitsunobu, O. Synthesis 1981, 1-28.