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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 14
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Original Articles

Chemo-enzymatic Preparations of (R)- and (S)-3-Iodocyclohex-2-en-1-yl Acetate

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Pages 2487-2496 | Received 22 May 2002, Published online: 20 Aug 2006

References

  • Mori , K. , Tamada , S. , Uchida , M. , Mizumachi , N. , Tachibana , Y. and Matsui , M. 1978 . Tetrahedron , 34 : 1901 – 1905 .
  • The pallado-catalyzed preparation of optically active (3-hydroxycyclohex-1-enyl)phosphonate was reported from enantiomerically enriched 3-bromocyclohex-2-en-1-ol: Attolini , M. , Bouguir , F. , Iacazio , G. , Peiffer , G. and Maffei , M. 2001 . Tetrahedron , 57 : 537 – 543 .
  • Barnier , J.-P. , Morisson , V. , Volle , I. and Blanco , L. 1999 . Tetrahedron: Asymmetry , 10 : 1107 – 1117 .
  • Enantiomeric excesses of (R)- and (S)-3-iodocyclohex-2-en-1-ol were determined after transformation to 3-methylcyclohex-2-en-1-ol (Seudenol), by 1H-NMR of the corresponding α-methoxy α-trifluoromethylphenylacetate and from its chiroptical properties
  • Paquette , L.A. , Elmore , S.W. , Combrink , K.D. , Hickey , E.R. and Rogers , R.D. 1992 . Helv. Chim. Acta , 75 : 1755 – 1771 .
  • c = ees/ees + eep; E = Ln[(1−ees)(eep/ees + eep)]/Ln[(1 + ees)(eep/ees + eep)]
  • Carrea , G. , Danieli , B. , Palmisano , G. , Riva , S. and Santagostino , M. 1992 . Tetrahedron: Asymmetry , 3 : 775 – 784 .
  • Johnson , C.R. and Sakaguchi , H. 1992 . Synlett , : 813 – 816 .
  • Piers , E. and Nagakura , I. 1975 . Synth. Commun. , 5 : 193 – 199 .
  • 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
  • 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 25 m column (0.25 mn id, gas carrier: helium P = 70 KPa, 80°C) the retention times were around 2 h but the separation of the enantiomers was not sufficient to obtain accurate measurements
  • Lallemand , J.-Y. , Leclaire , M. , Levet , R. and Aranda , G. 1993 . Tetrahedron: Asymmetry , 4 : 1775 – 1778 .
  • Mitsunobu , O. 1981 . Synthesis , : 1 – 28 .

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