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Both enantiomers of novel perfluoroalkane-tagged 5,5-diphenyl-2-oxazolidinone (DIOZ) auxiliaries have been prepared using a two-step one-pot synthesis, starting from commercially available N-(tert-butoxycarbonyl)-L-valine methyl ester. The key feature of this approach is the efficient generation of a suitably active perfluoroalkyl-aryllithium species. By use of this protocol, the perfluoroalkane-tagged DIOZ auxiliaries are obtained in high enantiomeric purity and on multigram scales with overall yields exceeding 50%. The perfluoroalkane-tagged auxiliaries enable the use of fluorous solid-phase extraction, allowing efficient purification of tagged intermediates from crude reaction mixtures. The new auxiliaries have been applied in an asymmetric synthesis of β-N-Fmoc-phenylalanine via a stereoselective conjugate addition.

Preparation of perfluoroalkane-tagged chiral auxiliaries and their application to stereoselective synthesis of a β2-amino acid building block