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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 19
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Original Articles

Enantioselective Hydrolysis of Racemic Acetates of Homoallyl Alcohols by Crude Pig Liver Acetone Powder (PLAP)

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Pages 2945-2949 | Received 23 Jul 1990, Published online: 24 Oct 2006

References

  • Brown , H. C. and Jadhav , P. K. 1983 . J. Am. Chem. Soc. , 105 : 2092
  • Roush , W. R. , Walts , A. E. and Hoong , L. K. 1985 . J. Am. Chem. Soc. , 107 : 8186
  • Hoffmann , R. W. 1988 . Pure & Appl. Chem. , 60 : 123
  • Masamune , S. 1988 . Pure & Appl. Chem. , 60 : 1587
  • Jones , J. B. 1986 . Tetrahedron , 42 : 3351
  • Kirchner , G. , Scollar , M. P. and Klibanov , A. M. 1985 . J. Am. Chem. Soc. , 107 : 7072
  • Gais , H. J. , Bulow , G. , Zatorski , A. , Jentsch , M. , Maidonis , P. and Hemmerle , H. 1989 . J. Org. Chem. , 54 : 5115
  • Basavaiah , D. , Krishna , P. Rama and Bharathi , T. K. in press . Tetrahedron Lett. ,
  • Adachi , K. , Kobayashi , S. and Ohno , M. 1986 . Chimia , 40 : 311 Crude PLAP was prepared from freshly purchased pig liver according to procedure of Ohno et al: ref.
  • We have also investigated the hydrolyses of chloroacetate and β-chloropropionate of 1-phenyl-3-buten-1-ol with PLAP but the results were not encouraging.
  • Hydrolysis (two phase: solvent/aq. buffer) was tried with other solvents such as toluene, methylene chloride but the results were not encouraging.
  • Petrier , C. and Luche , J. L. 1985 . J. Org. Chem. , 50 : 910 Homoallyl alcohols were prepared according to Luche's procedure: ref.
  • Minowa , N. and Mukaiyama , T. 1987 . Bull. Chem. Soc. Jpn. , 60 : 3697
  • We observed that different lots of PLAP show sometimes different activities (change in rate of hydrolysis). However, the enantioselectivity remains almost the same.

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