An Efficient Synthesis of Racemic and Optically Active Telluromethionine

References

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• This process was performed repeatedly with little success. It should be noted reference 6 did not report a yield for this step
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• During manuscript preparation a report by Krief et al., appeared describing a procedure employing sodium methyl selenolate and α-amino-γ-butyro-lactone for the construction of optically active selenomethionine. Krief, A. and Trabelsi, M., Synthetic Commun.1989, 19, 1203. L-Selenomethionine is also available from Sigma Chemical Co
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• This is essentially a titration of elemental tellurium with one equivalent of the appropriate alkyllithium. Upon formation of the tellurolate the solution mixture invariably changes from a dark opaque brown to a pale, clear yellow
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• Knapp6 reported that use of various acids did not promote crystallization. We have found that precipitation/purification is dependent on Te-Met concentration
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• The degree of racemization is currently being evaluated and will be reported elsewhere. Krief et al. 10 have reported that little racemization occurs with the use of the more basic selenolate anions. Based on Krief s results we feel that very little, if any, racemization has occurred
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• Luthra , N. P. and Odom , J. D. 1986 . “ The Chemistry of Organic Selenium and Tellurium Compounds ” . Edited by: Patai , S. and Rappoport , Z. Vol. 1 , 189 – 241 . New York : John Wiley and Sons . chapter 6
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• The yields typically ranged from 55–83%. It appears that the larger scale reaction (5 grams of α-amino-γ-butyrolactone) gives better results
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