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Org Lett. 2001 May 3;3(9):1285-6.

A novel synthesis of enantiomerically pure 5,5,5,5',5',5'-hexafluoroleucine.

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Department of Chemistry, Tufts University, 62 Talbot Avenue, Medford, Massachusetts 02155, USA.


[reaction in text] A novel, short, and efficient synthesis of (S)-5,5,5,5',5',5'-hexafluoroleucine (6) in greater than 99% ee starting from the protected oxazolidine aldehyde 1 is described. The enantiomeric excess of the product was calculated from an NMR analysis of a dipeptide formed by reaction with a protected L-serine derivative. Furthermore, a racemic sample of N-acylated hexafluoroleucine was enzymatically resolved by treatment with porcine kidney acylase I and was found to have the same optical rotation as a synthetic sample of 6.

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